Name: CIS-N-BENZYL-3-METHYLAMINO-4-METHYL-PIPERIDINE BIS-(HYDROCHLORIDE)
SKU: 1062580-52-2

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Basic Information

Molecular Structure:
CAS No.:	1062580-52-2
Name:	CIS-N-BENZYL-3-METHYLAMINO-4-METHYL-PIPERIDINE BIS-(HYDROCHLORIDE)

Formula:	C14H24Cl2N2
Molecular Weight:	291.264
Synonyms:	(3R,4R)-N,4-Dimethyl-1-(phenylmethyl)-3-piperidi;
Melting Point:	249～251℃
PSA:	15.27000
LogP:	4.04920

Synthetic route

: 477600-70-7
N-(3R,4R)-(1-benzyl-4-methylpiperidin-3-yl)-methylamine

: 1062580-52-2
N-((3R,4R)-1-benzyl-4-methylpiperidin-3-yl)-N-methylamine dihydrochloride

Conditions

Conditions	Yield
With hydrogenchloride In ethanol at 0 - 5℃; pH=3 - 4;	94%
With hydrogenchloride In n-heptane; isopropyl alcohol at 20℃; for 0.666667h; Reflux;	60%

: 32018-96-5
1-benzyl-4-methyl-piperidin-3-one

: 74-89-5
methylamine

: 1062580-52-2
N-((3R,4R)-1-benzyl-4-methylpiperidin-3-yl)-N-methylamine dihydrochloride

Conditions

Conditions	Yield
Stage #1: 1-benzyl-4-methyl-piperidin-3-one; methylamine With titanium tetrachloride; triethylamine In tetrahydrofuran at 20℃; for 4h; Stage #2: With sodium tris(acetoxy)borohydride; acetic acid In tetrahydrofuran at 25℃; Stage #3: With hydrogenchloride In ethanol	85%

: 32018-96-5
1-benzyl-4-methyl-piperidin-3-one

: 6998-30-7
methylamine acetate

A: 1062580-52-2
N-((3R,4R)-1-benzyl-4-methylpiperidin-3-yl)-N-methylamine dihydrochloride

B: (3R,4R)-1-benzyl-N,4-dimethylpiperidine-3-amine dihydrochloride

Conditions

Yield

Stage #1: 1-benzyl-4-methyl-piperidin-3-one; methylamine acetate With bis(1,5-cyclooctadiene)diiridium(I) dichloride; (S)-3,5-di-tert-butyl-4-methoxyphenyl-(6,6’-dimethoxybiphenyl-2,2’-diyl)-bis(diphenylphosphine); hydrogen In dichloromethane; isopropyl alcohol at 70℃; under 37503.8 Torr; for 18h;
Stage #2: With hydrogenchloride In dichloromethane; water; isopropyl alcohol Overall yield = 86%; Overall yield = 498 mg; enantioselective reaction;

A n/a
B 74%

...Expand

: 384338-23-2
(1-benzyl-4-methyl-piperidin-3-yl)-methyl-amine

A: 1062580-52-2
N-((3R,4R)-1-benzyl-4-methylpiperidin-3-yl)-N-methylamine dihydrochloride

B: (3R,4R)-1-benzyl-N,4-dimethylpiperidine-3-amine dihydrochloride

Conditions

Conditions	Yield
With hydrogenchloride In diethyl ether; acetone for 1h; Inert atmosphere; Overall yield = 498 mg;

: 32018-96-5
1-benzyl-4-methyl-piperidin-3-one

A: 1062580-52-2
N-((3R,4R)-1-benzyl-4-methylpiperidin-3-yl)-N-methylamine dihydrochloride

B: (3R,4R)-1-benzyl-N,4-dimethylpiperidine-3-amine dihydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: ethanol / 5 h / 20 °C / Inert atmosphere 2: hydrogen; bis(1,5-cyclooctadiene)diiridium(I) dichloride; (R)-diMe-PipPhos / isopropyl alcohol / 18 h / 20 °C / 37503.8 Torr / Glovebox; Inert atmosphere 3: hydrogenchloride / acetone; diethyl ether / 1 h / Inert atmosphere View Scheme

: C14H20N2

A: 1062580-52-2
N-((3R,4R)-1-benzyl-4-methylpiperidin-3-yl)-N-methylamine dihydrochloride

B: (3R,4R)-1-benzyl-N,4-dimethylpiperidine-3-amine dihydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrogen; bis(1,5-cyclooctadiene)diiridium(I) dichloride; (R)-diMe-PipPhos / isopropyl alcohol / 18 h / 20 °C / 37503.8 Torr / Glovebox; Inert atmosphere 2: hydrogenchloride / acetone; diethyl ether / 1 h / Inert atmosphere View Scheme

: methyl ((3R,4R)-1-benzyl-4-methylpiperidin-3-yl)carbamate

: 1062580-52-2
N-((3R,4R)-1-benzyl-4-methylpiperidin-3-yl)-N-methylamine dihydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 2.83 h / 0 °C / Reflux 2: hydrogenchloride / isopropyl alcohol; n-heptane / 0.67 h / 20 °C / Reflux View Scheme

: 923036-28-6
(1-benzyl-4-methyl-1,2,5,6-tetrahydropyridin-3-yl)carbamic acid methyl ester

: 1062580-52-2
N-((3R,4R)-1-benzyl-4-methylpiperidin-3-yl)-N-methylamine dihydrochloride

Conditions

Yield

Multi-step reaction with 3 steps
1: hydrogen; bis(1,5-cyclooctadiene)rhodium(I) trifluoromethanesulfonate; (R)-1-[(Sp)-2-(di-tert-butylphosphino)ferrocenyl]ethylbis(2-methylphenyl)phosphine / 2,2,2-trifluoroethanol / 6 h / 30 - 50 °C / 2625.26 Torr
2: lithium aluminium tetrahydride / tetrahydrofuran / 2.83 h / 0 °C / Reflux
3: hydrogenchloride / isopropyl alcohol; n-heptane / 0.67 h / 20 °C / Reflux
View Scheme

: 3430-27-1
3-amino-4-methylpyridine

: 1062580-52-2
N-((3R,4R)-1-benzyl-4-methylpiperidin-3-yl)-N-methylamine dihydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: dichloromethane; toluene / 10 h / 20 - 25 °C / Large scale 1.2: 70 - 80 °C / Large scale 1.3: 14 h / 10 °C / Large scale 2.1: hydrogenchloride / water; n-heptane / 70 - 75 °C / Large scale 2.2: 0 - 5 °C / Large scale 3.1: Di-p-toluoyl-L-tartaric acid / methanol / 1 h / 50 - 55 °C / Large scale 3.2: 2 h / pH 3 / Large scale View Scheme

: N-(1-benzyl-4-methyl-1,2,5,6-tetrahydropyridine-3-yl)acetylamine

: 1062580-52-2
N-((3R,4R)-1-benzyl-4-methylpiperidin-3-yl)-N-methylamine dihydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: hydrogenchloride / water; n-heptane / 70 - 75 °C / Large scale 1.2: 0 - 5 °C / Large scale 2.1: Di-p-toluoyl-L-tartaric acid / methanol / 1 h / 50 - 55 °C / Large scale 2.2: 2 h / pH 3 / Large scale View Scheme