1,1'-Carbonyldiimidazole → Tert-butyl 4-(2-oxo-1,2,4,5-tetrahydrobenzo[d][1,3]diazepin-3-yl)piperidine-1-carboxylate

HRID 1671592Notes

Reaction equation

HRID 1671592 reaction equation
[C:1](N1C=CN=C1)(N1C=CN=C1)=[O:2].[NH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH2:20][CH2:21][NH:22][CH:23]1[CH2:28][CH2:27][N:26]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:25][CH2:24]1>CN(C)C=O.C(OCC)(=O)C>[C:32]([O:31][C:29]([N:26]1[CH2:27][CH2:28][CH:23]([N:22]2[CH2:21][CH2:20][C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=3[NH:13][C:1]2=[O:2])[CH2:24][CH2:25]1)=[O:30])([CH3:35])([CH3:34])[CH3:33]

Participants

5

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 18444264Tert-butyl 4-{[2-(2-aminophenyl)ethyl]amino}piperidine-1-carboxylate

Product 1

HCID 58823744Tert-butyl 4-(2-oxo-1,2,4,5-tetrahydrobenzo[d][1,3]diazepin-3-yl)piperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Carbonyldiimidazole (8.73 g, 53.8 mmol) was added to a solution of tert-butyl 4-{[2-(2-aminophenyl)ethyl]amino}piperidine-1-carboxylate (17.2 g, 53.8 mmol) in dimethylformamide (200 mL), and stirred at room temperature for 2 h. The reaction was diluted with ethyl acetate and extracted with water, then saturated brine. The crude product was purified by chromatography (silica gel, 0-30% ethyl acetate in methylene chloride gradient elution). The title compound was obtained as a dark solid (4.8 g).

Workup

  1. extractionextracted with water
  2. customThe crude product was purified by chromatography (silica gel, 0-30% ethyl acetate in methylene chloride gradient elution)

Sources & evidence

ORD record
ord-05a234eef41d410dbc54fde7e8a834c7
Source dataset
uspto-grants-2011_08
Patent number
US07994325B2

Reaction notes

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