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

HRID 1695889Notes

Reaction equation

HRID 1695889 reaction equation
[NH2:1][C:2]1[CH:23]=[CH:22][CH:21]=[CH:20][C:3]=1[CH2:4][CH2:5][NH:6][CH:7]1[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]1.C1N=CN([C:29](N2C=NC=C2)=[O:30])C=1>CN(C=O)C.O>[O:30]=[C:29]1[NH:1][C:2]2[CH:23]=[CH:22][CH:21]=[CH:20][C:3]=2[CH2:4][CH2:5][N:6]1[CH:7]1[CH2:8][CH2:9][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:17])[CH3:18])=[O:14])[CH2:11][CH2:12]1

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 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of tert-butyl 4-(2-aminophenethylamino)piperidine-1-carboxylate (6.9 g, 30 mmol) in DMF (110 ml) was added CDI (4.86 g, 30 mmol) in portions followed by stirring the reaction mixture at RT for 2 h. The reaction mixture was diluted with water and extracted with EtOAc. The organics were combined, washed with water, brine, and evaporated to dryness to give the desired product. LC/MS (10% to 99%): M/Z (M+H)+ (obs)=346; tR=3.24.

Workup

  1. extractionextracted with EtOAc
  2. washwashed with water, brine
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-46696c2d8d464311ae5b4e984caf4a13
Source dataset
uspto-grants-2012_04
Patent number
US08163737B2

Reaction notes

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