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Benzylamine → 1-methyl-4-phenyl-N-(phenylmethyl)-4-piperidinecarboxamide

HRID 7408
Notes
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Reaction equation

HRID 7408 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][C:5]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)([C:8](Cl)=[O:9])[CH2:4][CH2:3]1.[C:17]1([CH2:23][NH2:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(N(CC)CC)C.C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl.O>[CH3:1][N:2]1[CH2:7][CH2:6][C:5]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)([C:8]([NH:24][CH2:23][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:9])[CH2:4][CH2:3]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 7504BenzylamineHCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 219902151-Methyl-4-phenyl-4-piperidinecarbonyl chloride

Product 1

HCID 219902061-methyl-4-phenyl-N-(phenylmethyl)-4-piperidinecarboxamideYield 95.3%

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 6344DichloromethaneSolvent

Procedure

1-Methyl-4-phenyl-4-piperidinecarbonyl chloride (0.49 mol) was added portionwise at room temperature to a stirring mixture of benzenemethanamine (0.49 mol) and triethyl amine (1.223 mol) in CH2Cl2 (2500 ml). The mixture was stirred at room temperature for 1 hour. K2CO3 (150 g) and H2O were added. The mixture was stirred and separated into its layers. The aqueous layer was extracted with CH2Cl2. The combined organic layer was dried (MgSO4), filtered and the solvent was evaporated, yielding 144 g of 1-methyl-4-phenyl-N-(phenylmethyl)-4-piperidinecarboxamide (95%) (interm. 12).

Workup

  1. stirringThe mixture was stirred
  2. customseparated into its layers
  3. extractionThe aqueous layer was extracted with CH2Cl2
  4. dry with materialThe combined organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-208c125703734caba2a9259dcaadb6cc
Source dataset
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07087595B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes