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4-Benzylpiperidine
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Name

4-Benzylpiperidine

 EINECS 250-535-0
CAS No. 31252-42-3 Density 0.969 g/cm3
PSA 12.03000 LogP 2.55750
Solubility N/A Melting Point 6-7 °C(lit.)
Formula C12H17N Boiling Point 279.6 °C at 760 mmHg
Molecular Weight 175.274 Flash Point 125.4 °C
Transport Information N/A Appearance CLEAR COLOURLESS TO YELLOW VISCOUS LIQUID
Safety 26-36 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 31252-42-3 (4-BENZYLPIPERIDINE) Hazard Symbols IrritantXi
Synonyms

Piperidine,4-benzyl- (6CI,7CI,8CI);4-(Phenylmethyl)piperidine;4-Benzylpiperidine;NSC30346;

Article Data 22

4-Benzylpiperidine Synthetic route

205641-99-2

4-benzyl-1-[(4-methylphenyl)sulfonyl]piperidine

31252-42-3

4-benzylpyperidine

Conditions
ConditionsYield
Stage #1: 4-benzyl-1-[(4-methylphenyl)sulfonyl]piperidine With Na/K absorbed into silica gel In tetrahydrofuran at 20℃; Inert atmosphere;
Stage #2: With water In tetrahydrofuran		96%
92%
With dimethyl(phenyl)silyl lithium In tetrahydrofuran at 0℃;78%
110-89-4

piperidine

100-52-7

benzaldehyde

31252-42-3

4-benzylpyperidine

Conditions
ConditionsYield
With sodium tetrahydroborate; cetyltrimethylammonim bromide at 20℃; for 14h;96%
544478-05-9

4-benzyl-N-tritylpiperidine

31252-42-3

4-benzylpyperidine

Conditions
ConditionsYield
Stage #1: 4-benzyl-N-tritylpiperidine With naphthalene; lithium In tetrahydrofuran at 0℃; for 1h;
Stage #2: With water In tetrahydrofuran at 0 - 20℃;		91%
15104-07-1

1-nitroso-4-(phenylmethyl)piperidine

31252-42-3

4-benzylpyperidine

Conditions
ConditionsYield
With sodium tetrahydroborate; titanium tetrachloride In 1,2-dimethoxyethane for 14h; Ambient temperature;90%
With sodium tetrahydroborate; nickel dichloride In tetrahydrofuran for 6h; Ambient temperature;90%

4-benzyl-N-(triphenylsilyl)piperidine

31252-42-3

4-benzylpyperidine

Conditions
ConditionsYield
With naphthalene; lithium In tetrahydrofuran; methanol at 20℃; for 5h;89%
132251-82-2

4-benzyl-1-(methanesulfonyl)piperidine

31252-42-3

4-benzylpyperidine

Conditions
ConditionsYield
Stage #1: 4-benzyl-1-(methanesulfonyl)piperidine With Na/K absorbed into silica gel In tetrahydrofuran at 20℃; Inert atmosphere;
Stage #2: With water In tetrahydrofuran		89%
Product distribution / selectivity;83%
2116-65-6

4-benzyl pyridine

A

78197-28-1

4-Cyclohexylmethyl-piperidine

B

31252-42-3

4-benzylpyperidine

Conditions
ConditionsYield
With hydrogenchloride; platinum Hydrogenation;
2116-65-6

4-benzyl pyridine

31252-42-3

4-benzylpyperidine

Conditions
ConditionsYield
With ethanol; sodium
With acetic acid; platinum Hydrogenation;
With nickel at 100℃; under 110326 - 220652 Torr; Hydrogenation;
With platinum(IV) oxide; hydrogen In acetic acid at 20℃; under 2585.81 Torr; for 12h;
Stage #1: 4-benzyl pyridine With hydrogen; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane In octane at 120℃; under 15001.5 Torr; for 40h;
Stage #2: With water Catalytic behavior; chemoselective reaction;		> 99 %Chromat.
2116-65-6

4-benzyl pyridine

64-17-5

ethanol

sodium

sodium

A

31252-42-3

4-benzylpyperidine

B

4-benzyl-piperideine

4-benzyl-piperideine

1-(4-benzylpiperidin-1-yl)-2,2-dimethylpropan-1-one

31252-42-3

4-benzylpyperidine

Conditions
ConditionsYield
With naphthalene; lithium In tetrahydrofuran at 0℃; for 1h;95 % Chromat.

4-Benzylpiperidine Chemical Properties

IUPAC Name: Piperidine, 4-(phenylmethyl)-
The MF of Piperidine, 4-(phenylmethyl)- (31252-42-3) is C12H17N.

                        
The MW of Piperidine, 4-(phenylmethyl)- (31252-42-3) is 175.27.
Synonyms of Piperidine, 4-(phenylmethyl)- (31252-42-3): 4-Benzylpiperidine ; Piperidine, 4- (phenylmethyl)- ; 4-(Phenylmethyl)piperidine ; 4-Benzyl-piperidine ; Phenyl(4-piperidyl)methane ; Piperidine, 4-benzyl- 
Product Categories: Piperidine;Piperidine Series
Form: clear colourless to yellow viscous liquid
Index of Refraction: 1.526 
EINECS: 250-535-0
Density: 0.969 g/ml 
Flash Point: 125.4 °C
Boiling Point: 279.6 °C
Melting Point: 6-7 °C
BRN: 132339

4-Benzylpiperidine Uses

    Piperidine, 4-(phenylmethyl)- (31252-42-3) is used as pharmaceutical Intermediates.

4-Benzylpiperidine Production

Treatment of 2,5-dihydroxybenzoic acid (I) with dimethyl sulfate and K2CO3 afforded methyl 2-hydroxy-5-methoxybenzoate (II). Condensation of (II) with dimethylthiocarbamoyl chloride gave the O-aryl thiocarbamate (III), which underwent thermal rearrangement to the S-aryl isomer (IV) upon heating at 265 C in diphenyl ether. Subsequent hydrolysis of the thiocarbamate group of (IV) furnished the desired thiophenol compound (V). Cyclization of the mercapto ester (V) with 2-chloroethylamine (VI) gave rise to the benzothiazepinone (VII), which was further reduced to the benzothiazepine (VIII) using LiAlH4. Acylation of (VIII) with acryloyl chloride (IX) provided the acrylamide (X). Finally, Michael addition of 4-benzylpiperidine (XI) to acrylamide (X) yielded the title compound.

4-Benzylpiperidine Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intravenous 56mg/kg (56mg/kg)   U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#01587,

4-Benzylpiperidine Safety Profile

Safety information of Piperidine, 4-(phenylmethyl)- (31252-42-3):
Hazard Codes  Xi
Risk Statements 
36/37/38  Irritating to eyes, respiratory system and skin
Safety Statements 
26  In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36  Wear suitable protective clothing
WGK Germany  3
RTECS  TM4728000
Hazard Note  Irritant

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