1,1'-Carbonyldiimidazole → HCID 21268366, compound

HRID 565602Notes

Reaction equation

HRID 565602 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11](C2C=CC=C(C)C=2)([CH2:14][NH2:15])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:23]([N:30]1[CH:34]=[CH:33]N=C1)(N1C=CN=C1)=[O:24]>ClCCl>[CH2:1]([N:8]1[CH2:9][CH2:10][C:11]2([N:30]([C:34]3[CH:33]=[CH:4][CH:3]=[C:2]([CH3:7])[CH:1]=3)[C:23](=[O:24])[NH:15][CH2:14]2)[CH2:12][CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 21268362HCID 21268362, compound

Product 1

HCID 21268366HCID 21268366, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-benzyl-4-(3-methylphenyl)-4-aminomethyl-piperidine (0.52 g, 1.67 mmol) and 1,1′-carbonyldiimidazole (0.41 g, 2.5 mmol) in dichloromethane (2 mL) was stirred at room temp. for 3 days. The resultant solution was concentrated and the residue subjected to column chromatography on silica gel eluting with a 1:1 mixture of chloroform and chloroform saturated with ammonia gas. Collection and concentration of appropriate fractions provide the title compound. FAB MS m/e 336 (M+1)

Workup

  1. concentrationThe resultant solution was concentrated
  2. additionthe residue subjected to column chromatography on silica gel eluting with a 1:1 mixture of chloroform and chloroform saturated with ammonia gas
  3. customCollection and concentration of appropriate fractions

Sources & evidence

ORD record
ord-34f6f41d89c24beca34d192c344ad920
Source dataset
uspto-grants-2001_01
Patent number
US06172076B2

Reaction notes

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