Benzylamine → HCID 11278060, compound

HRID 2106199Notes

Reaction equation

HRID 2106199 reaction equation
C(OC([N:8]1[CH2:14][CH2:13][C:12]2[C:15]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[CH:16][N:17]([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:11]=2[CH2:10][CH2:9]1)=O)(C)(C)C.C(N)C1C=CC=CC=1>C1C=CC=CC=1>[CH2:18]([N:17]1[C:11]2[CH2:10][CH2:9][NH:8][CH2:14][CH2:13][C:12]=2[C:15]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:16]1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 67268982HCID 67268982, compound

Product 1

HCID 11278060HCID 11278060, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

1-Benzyl-3-phenyl-4,5,7,8-tetrahydro-1H-pyrrolo[2,3-d]azepine-6-carboxylic acid tert-butyl ester. A solution of the compound (0.53 g) from Example 59, Step B, and 272 μL of benzylamine in benzene (10 mL) was heated at reflux for 24 h using a Dean-Stark apparatus. The solvent was removed, the crude material was dissolved in toluene (10 mL), and 0.38 g of (2-nitro-vinyl)-benzene was added. The mixture was stirred for 24 h at RT and concentrated in vacuo. Chromatography on SiO2 (1 to 20% EtOAc/hexanes) afforded 108.0 mg of the desired compound. MS (ESI): exact mass calculated for C26H30N2O2, 402.53; found, m/z 403.2 [M+H]+.

Workup

  1. temperatureat reflux for 24 h
  2. customThe solvent was removed
  3. dissolutionthe crude material was dissolved in toluene (10 mL)
  4. addition0.38 g of (2-nitro-vinyl)-benzene was added
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4cae5aa6f5624ee782b04394f494d3b7
Source dataset
uspto-grants-2009_08
Patent number
US07579470B2

Reaction notes

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