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Basic Information

Molecular Structure:
CAS No.:	86541-74-4
Name:	Benazepril hydrochloride
Article Data:	13

Formula:	C₂₄H₂₉ClN₂O₅
Molecular Weight:	460.958
Synonyms:	1H-1-Benzazepine-1-aceticacid,3-[[(1S)-1-(ethoxycarbonyl)-3-phenylpropyl]amino]-2,3,4,5-tetrahydro-2-oxo-,monohydrochloride, (3S)- (9CI);1H-1-Benzazepine-1-acetic acid,3-[[1-(ethoxycarbonyl)-3-phenylpropyl]amino]-2,3,4,5-tetrahydro-2-oxo-,monohydrochloride, [S-(R,R)]-;CGS 14824A;CGS14824A HCl;Lotensin;Lotension;
EINECS:	630-414-2
Melting Point:	188-190 °C
Boiling Point:	691.2 °C at 760 mmHg
Flash Point:	371.8 °C
Solubility:	DMSO: ~34 mg/mL, soluble
Appearance:	crystalline solid
Safety:	22-24/25
PSA:	95.94000
LogP:	3.83100

Synthetic route

: 109010-61-9
(2S,3'S)-2-(1-tert-butoxycarbonylmethyl-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-3-ylamino)-4-phenylbutyric acid ethyl ester

: 86541-74-4
benazepril hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride In ethyl acetate	91.6%
With hydrogenchloride In toluene at 0 - 20℃; for 1.5h;	90%
With hydrogenchloride In ethyl acetate at -10 - 25℃; for 16h; Industry scale;
With hydrogenchloride In ethyl acetate at 10℃; under 760.051 Torr; Solvent; Reflux;	Ca. 114 g
With hydrogenchloride In Isopropyl acetate at 10℃;	99.6 g

: ethyl (S)-2-(((S)-1-(2-(benzyloxy)-2-oxoethyl)-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-3- yl)amino)-4-phenylbutanoate

: 86541-74-4
benazepril hydrochloride

Conditions

Conditions	Yield
Stage #1: ethyl (S)-2-(((S)-1-(2-(benzyloxy)-2-oxoethyl)-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-3- yl)amino)-4-phenylbutanoate With palladium 10% on activated carbon; hydrogen In ethanol at 20℃; for 3h; Stage #2: With hydrogenchloride In ethyl acetate; acetone Reflux;	91%

: 64920-29-2
2-oxo-4-phenylbutanoic acid ethyl ester

: 86499-53-8
(3S)-3-amino-1-(carboxymethyl)-2,3,4,5-tetrahydro-1H-<1>benzazepin-2-one sodium salt

A: 86541-74-4
benazepril hydrochloride

B: 86541-77-7
(3S)-1-(carboxymethyl)-<<(1S)-1-(ethoxycarbonyl)-3-phenylpropyl>amino>-2,3,4,5-tetrahydro-1H-<1>benzazepin-2-one hydrochloride

Conditions

Conditions	Yield
With sodium cyanoborohydride In methanol; acetic acid Ambient temperature;	A 12% B 25%

...Expand

: 577-59-3
2-acetylnitrobenzene

: 86541-74-4
benazepril hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1.1: 99 percent / sodium ethoxide / tetrahydrofuran / 2 h / 0 °C 2.1: phenacyl chloride; baker's yeast / diethyl ether; H2O / 24 h / 30 °C 3.1: H2; HCl / Pd/C / methanol / 20 °C 3.2: 42 percent / AcOH / toluene / 80 °C 4.1: Et3N / tetrahydrofuran / 16 h / 20 °C 5.1: 78 percent / 1,2-dimethoxy-ethane / 60 h / 50 °C 6.1: tetrabutylammonium bromide; KOH / tetrahydrofuran / 0.5 h / 0 °C 6.2: 98 percent / tetrahydrofuran / 5 h / 20 °C 7.1: 90 percent / HCl / toluene / 1.5 h / 0 - 20 °C View Scheme
Multi-step reaction with 8 steps 1.1: 99 percent / sodium ethoxide / tetrahydrofuran / 2 h / 0 °C 2.1: phenacyl chloride; baker's yeast / diethyl ether; H2O / 24 h / 30 °C 3.1: NaBH4; acetic acid / 2 h / 0 °C 4.1: H2 / Pd/C / methanol / 24 h / 20 °C 4.2: H2; hydrochloric acid / Pd/C / methanol / 36 h / 20 °C 4.3: 74 percent / AcOH / toluene / 16 h / 80 °C 5.1: Et3N / tetrahydrofuran / 16 h / 20 °C 6.1: 78 percent / 1,2-dimethoxy-ethane / 60 h / 50 °C 7.1: tetrabutylammonium bromide; KOH / tetrahydrofuran / 0.5 h / 0 °C 7.2: 98 percent / tetrahydrofuran / 5 h / 20 °C 8.1: 90 percent / HCl / toluene / 1.5 h / 0 - 20 °C View Scheme

Yield

Multi-step reaction with 7 steps
1.1: 99 percent / sodium ethoxide / tetrahydrofuran / 2 h / 0 °C
2.1: phenacyl chloride; baker's yeast / diethyl ether; H2O / 24 h / 30 °C
3.1: H2; HCl / Pd/C / methanol / 20 °C
3.2: 42 percent / AcOH / toluene / 80 °C
4.1: Et3N / tetrahydrofuran / 16 h / 20 °C
5.1: 78 percent / 1,2-dimethoxy-ethane / 60 h / 50 °C
6.1: tetrabutylammonium bromide; KOH / tetrahydrofuran / 0.5 h / 0 °C
6.2: 98 percent / tetrahydrofuran / 5 h / 20 °C
7.1: 90 percent / HCl / toluene / 1.5 h / 0 - 20 °C
View Scheme

Multi-step reaction with 8 steps
1.1: 99 percent / sodium ethoxide / tetrahydrofuran / 2 h / 0 °C
2.1: phenacyl chloride; baker's yeast / diethyl ether; H2O / 24 h / 30 °C
3.1: NaBH4; acetic acid / 2 h / 0 °C
4.1: H2 / Pd/C / methanol / 24 h / 20 °C
4.2: H2; hydrochloric acid / Pd/C / methanol / 36 h / 20 °C
4.3: 74 percent / AcOH / toluene / 16 h / 80 °C
5.1: Et3N / tetrahydrofuran / 16 h / 20 °C
6.1: 78 percent / 1,2-dimethoxy-ethane / 60 h / 50 °C
7.1: tetrabutylammonium bromide; KOH / tetrahydrofuran / 0.5 h / 0 °C
7.2: 98 percent / tetrahydrofuran / 5 h / 20 °C
8.1: 90 percent / HCl / toluene / 1.5 h / 0 - 20 °C
View Scheme

: 178114-28-8
4-(2-nitrophenyl)-2,4-dioxobutanoic acid ethyl ester

: 86541-74-4
benazepril hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1.1: phenacyl chloride; baker's yeast / diethyl ether; H2O / 24 h / 30 °C 2.1: H2; HCl / Pd/C / methanol / 20 °C 2.2: 42 percent / AcOH / toluene / 80 °C 3.1: Et3N / tetrahydrofuran / 16 h / 20 °C 4.1: 78 percent / 1,2-dimethoxy-ethane / 60 h / 50 °C 5.1: tetrabutylammonium bromide; KOH / tetrahydrofuran / 0.5 h / 0 °C 5.2: 98 percent / tetrahydrofuran / 5 h / 20 °C 6.1: 90 percent / HCl / toluene / 1.5 h / 0 - 20 °C View Scheme
Multi-step reaction with 7 steps 1.1: phenacyl chloride; baker's yeast / diethyl ether; H2O / 24 h / 30 °C 2.1: NaBH4; acetic acid / 2 h / 0 °C 3.1: H2 / Pd/C / methanol / 24 h / 20 °C 3.2: H2; hydrochloric acid / Pd/C / methanol / 36 h / 20 °C 3.3: 74 percent / AcOH / toluene / 16 h / 80 °C 4.1: Et3N / tetrahydrofuran / 16 h / 20 °C 5.1: 78 percent / 1,2-dimethoxy-ethane / 60 h / 50 °C 6.1: tetrabutylammonium bromide; KOH / tetrahydrofuran / 0.5 h / 0 °C 6.2: 98 percent / tetrahydrofuran / 5 h / 20 °C 7.1: 90 percent / HCl / toluene / 1.5 h / 0 - 20 °C View Scheme

Yield

Multi-step reaction with 6 steps
1.1: phenacyl chloride; baker's yeast / diethyl ether; H2O / 24 h / 30 °C
2.1: H2; HCl / Pd/C / methanol / 20 °C
2.2: 42 percent / AcOH / toluene / 80 °C
3.1: Et3N / tetrahydrofuran / 16 h / 20 °C
4.1: 78 percent / 1,2-dimethoxy-ethane / 60 h / 50 °C
5.1: tetrabutylammonium bromide; KOH / tetrahydrofuran / 0.5 h / 0 °C
5.2: 98 percent / tetrahydrofuran / 5 h / 20 °C
6.1: 90 percent / HCl / toluene / 1.5 h / 0 - 20 °C
View Scheme

Multi-step reaction with 7 steps
1.1: phenacyl chloride; baker's yeast / diethyl ether; H2O / 24 h / 30 °C
2.1: NaBH4; acetic acid / 2 h / 0 °C
3.1: H2 / Pd/C / methanol / 24 h / 20 °C
3.2: H2; hydrochloric acid / Pd/C / methanol / 36 h / 20 °C
3.3: 74 percent / AcOH / toluene / 16 h / 80 °C
4.1: Et3N / tetrahydrofuran / 16 h / 20 °C
5.1: 78 percent / 1,2-dimethoxy-ethane / 60 h / 50 °C
6.1: tetrabutylammonium bromide; KOH / tetrahydrofuran / 0.5 h / 0 °C
6.2: 98 percent / tetrahydrofuran / 5 h / 20 °C
7.1: 90 percent / HCl / toluene / 1.5 h / 0 - 20 °C
View Scheme

: 46460-23-5
ethyl 2-amino-4-phenyl-(2S)-butyrate

: 86541-74-4
benazepril hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: 78 percent / 1,2-dimethoxy-ethane / 60 h / 50 °C 2.1: tetrabutylammonium bromide; KOH / tetrahydrofuran / 0.5 h / 0 °C 2.2: 98 percent / tetrahydrofuran / 5 h / 20 °C 3.1: 90 percent / HCl / toluene / 1.5 h / 0 - 20 °C View Scheme

: 608148-60-3
(3R)-3-hydroxy-1,3,4,5-tetrahydrobenzo[b]azepin-2-one

: 86541-74-4
benazepril hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: Et3N / tetrahydrofuran / 16 h / 20 °C 2.1: 78 percent / 1,2-dimethoxy-ethane / 60 h / 50 °C 3.1: tetrabutylammonium bromide; KOH / tetrahydrofuran / 0.5 h / 0 °C 3.2: 98 percent / tetrahydrofuran / 5 h / 20 °C 4.1: 90 percent / HCl / toluene / 1.5 h / 0 - 20 °C View Scheme

: 608148-58-9
(2R)-2-hydroxy-4-(2-nitrophenyl)-4-oxobutyric acid ethyl ester

: 86541-74-4
benazepril hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: H2; HCl / Pd/C / methanol / 20 °C 1.2: 42 percent / AcOH / toluene / 80 °C 2.1: Et3N / tetrahydrofuran / 16 h / 20 °C 3.1: 78 percent / 1,2-dimethoxy-ethane / 60 h / 50 °C 4.1: tetrabutylammonium bromide; KOH / tetrahydrofuran / 0.5 h / 0 °C 4.2: 98 percent / tetrahydrofuran / 5 h / 20 °C 5.1: 90 percent / HCl / toluene / 1.5 h / 0 - 20 °C View Scheme
Multi-step reaction with 6 steps 1.1: NaBH4; acetic acid / 2 h / 0 °C 2.1: H2 / Pd/C / methanol / 24 h / 20 °C 2.2: H2; hydrochloric acid / Pd/C / methanol / 36 h / 20 °C 2.3: 74 percent / AcOH / toluene / 16 h / 80 °C 3.1: Et3N / tetrahydrofuran / 16 h / 20 °C 4.1: 78 percent / 1,2-dimethoxy-ethane / 60 h / 50 °C 5.1: tetrabutylammonium bromide; KOH / tetrahydrofuran / 0.5 h / 0 °C 5.2: 98 percent / tetrahydrofuran / 5 h / 20 °C 6.1: 90 percent / HCl / toluene / 1.5 h / 0 - 20 °C View Scheme

Yield

Multi-step reaction with 5 steps
1.1: H2; HCl / Pd/C / methanol / 20 °C
1.2: 42 percent / AcOH / toluene / 80 °C
2.1: Et3N / tetrahydrofuran / 16 h / 20 °C
3.1: 78 percent / 1,2-dimethoxy-ethane / 60 h / 50 °C
4.1: tetrabutylammonium bromide; KOH / tetrahydrofuran / 0.5 h / 0 °C
4.2: 98 percent / tetrahydrofuran / 5 h / 20 °C
5.1: 90 percent / HCl / toluene / 1.5 h / 0 - 20 °C
View Scheme

Multi-step reaction with 6 steps
1.1: NaBH4; acetic acid / 2 h / 0 °C
2.1: H2 / Pd/C / methanol / 24 h / 20 °C
2.2: H2; hydrochloric acid / Pd/C / methanol / 36 h / 20 °C
2.3: 74 percent / AcOH / toluene / 16 h / 80 °C
3.1: Et3N / tetrahydrofuran / 16 h / 20 °C
4.1: 78 percent / 1,2-dimethoxy-ethane / 60 h / 50 °C
5.1: tetrabutylammonium bromide; KOH / tetrahydrofuran / 0.5 h / 0 °C
5.2: 98 percent / tetrahydrofuran / 5 h / 20 °C
6.1: 90 percent / HCl / toluene / 1.5 h / 0 - 20 °C
View Scheme

: 656830-87-4
(R)-2,4-Dihydroxy-4-(2-nitro-phenyl)-butyric acid ethyl ester

: 86541-74-4
benazepril hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: H2 / Pd/C / methanol / 24 h / 20 °C 1.2: H2; hydrochloric acid / Pd/C / methanol / 36 h / 20 °C 1.3: 74 percent / AcOH / toluene / 16 h / 80 °C 2.1: Et3N / tetrahydrofuran / 16 h / 20 °C 3.1: 78 percent / 1,2-dimethoxy-ethane / 60 h / 50 °C 4.1: tetrabutylammonium bromide; KOH / tetrahydrofuran / 0.5 h / 0 °C 4.2: 98 percent / tetrahydrofuran / 5 h / 20 °C 5.1: 90 percent / HCl / toluene / 1.5 h / 0 - 20 °C View Scheme

Yield

Multi-step reaction with 5 steps
1.1: H2 / Pd/C / methanol / 24 h / 20 °C
1.2: H2; hydrochloric acid / Pd/C / methanol / 36 h / 20 °C
1.3: 74 percent / AcOH / toluene / 16 h / 80 °C
2.1: Et3N / tetrahydrofuran / 16 h / 20 °C
3.1: 78 percent / 1,2-dimethoxy-ethane / 60 h / 50 °C
4.1: tetrabutylammonium bromide; KOH / tetrahydrofuran / 0.5 h / 0 °C
4.2: 98 percent / tetrahydrofuran / 5 h / 20 °C
5.1: 90 percent / HCl / toluene / 1.5 h / 0 - 20 °C
View Scheme

: 4-(2-nitro-phenyl)-2,4-dioxo-butyric acid butyl ester

: 86541-74-4
benazepril hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: phenacyl chloride; baker's yeast / diethyl ether; H2O / 24 h / 30 °C 1.2: H2; hydrochloric acid / Pd/C / methanol / 20 °C 1.3: AcOH / toluene / 80 °C 2.1: Et3N / tetrahydrofuran / 16 h / 20 °C 3.1: 78 percent / 1,2-dimethoxy-ethane / 60 h / 50 °C 4.1: tetrabutylammonium bromide; KOH / tetrahydrofuran / 0.5 h / 0 °C 4.2: 98 percent / tetrahydrofuran / 5 h / 20 °C 5.1: 90 percent / HCl / toluene / 1.5 h / 0 - 20 °C View Scheme

Yield

Multi-step reaction with 5 steps
1.1: phenacyl chloride; baker's yeast / diethyl ether; H2O / 24 h / 30 °C
1.2: H2; hydrochloric acid / Pd/C / methanol / 20 °C
1.3: AcOH / toluene / 80 °C
2.1: Et3N / tetrahydrofuran / 16 h / 20 °C
3.1: 78 percent / 1,2-dimethoxy-ethane / 60 h / 50 °C
4.1: tetrabutylammonium bromide; KOH / tetrahydrofuran / 0.5 h / 0 °C
4.2: 98 percent / tetrahydrofuran / 5 h / 20 °C
5.1: 90 percent / HCl / toluene / 1.5 h / 0 - 20 °C
View Scheme

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Specification

The Benazepril hydrochloride, with the CAS registry number 86541-74-4, is also known as (3S)-3-(((1S)-1-Carboxy-3-phenylpropyl)amino)-2,3,4,5-tetrahydro-2-oxo-1H-1-benzazepine-1-acetic acid, 3-ethyl ester, monohydrochloride; Benazepril HCl; Cibacen; Cibacen CHF; Labopol. It belongs to the product categories of Intermediates & Fine Chemicals; Pharmaceuticals; Amines; Aromatics; Heterocycles. This chemical's molecular formula is C₂₄H₂₉ClN₂O₅ and molecular weight is 460.96. What's more, its IUPAC name 2-[(3S)-3-[[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino]-2-oxo-4,5-dihydro-3H-1-benzazepin-1-yl]acetic acid hydrochloride. In addition, Benazepril hydrochloride (CAS 86541-74-4) is crystalline solid which is soluble in DMSO. It is used in high blood pressure and congestive heart failure. When you are using this chemical, you should not breathe dust and avoid contact with skin and eyes.

Physical properties about Benazepril hydrochloride (CAS 86541-74-4) are: (1)ACD/LogP: 3.864; (2)# of Rule of 5 Violations: 0; (3)#H bond acceptors: 7; (4)#H bond donors: 2; (5)#Freely Rotating Bonds: 10; (6)Polar Surface Area: 76.15 Å²; (7)Flash Point: 371.8 °C; (8)Enthalpy of Vaporization: 106.37 kJ/mol; (9)Boiling Point: 691.2 °C at 760 mmHg; (10)Vapour Pressure: 4.69E-20 mmHg at 25°C.

Preparation of Benazepril hydrochloride (CAS 86541-74-4): The reaction of 2(R)-hydroxy-4-phenyl butyric acid ethyl ester (I) with trifluoromethanesulfonic anhydride in dichloromethane gives the corresponding triflate (II), which is then condensed with the amino benzazepinone (III) by means of NMM in the same solvent to provide the target benazepril.

Benazepril hydrochloride can be produced by 2(R)-hydroxy-4-phenyl butyric acid ethyl ester (I) and trifluoromethanesulfonic anhydride.

You can still convert the following datas of Benazepril hydrochloride (CAS 86541-74-4) into molecular structure:
(1) SMILES:Cl.O=C(OCC)[C@@H](N[C@@H]2C(=O)N(c1ccccc1CC2)CC(=O)O)CCc3ccccc3
(2) Std. InChI:InChI=1S/C24H28N2O5.ClH/c1-2-31-24(30)20(14-12-17-8-4-3-5-9-17)25-19-15-13-18-10-6-7-11-21(18)26(23(19)29)16-22(27)28;/h3-11,19-20,25H,2,12-16H2,1H3,(H,27,28);1H/t19-,20-;/m0./s1
(3) Std. InChIKey:VPSRQEHTHIMDQM-FKLPMGAJSA-N

The following are the toxicity data of Benazepril hydrochloride (CAS 86541-74-4) which has been tested.

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
dog	LDLo	oral	1gm/kg (1000mg/kg)	SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION BEHAVIORAL: FOOD INTAKE (ANIMAL) GASTROINTESTINAL: NAUSEA OR VOMITING	Cardiovascular Drug Reviews. Vol. 8, Pg. 89, 1990.
mouse	LD50	oral	4019mg/kg (4019mg/kg)		Cardiovascular Drug Reviews. Vol. 8, Pg. 89, 1990.
rat	LD50	oral	> 5gm/kg (5000mg/kg)		Cardiovascular Drug Reviews. Vol. 8, Pg. 89, 1990.