Trifluoroacetic acid → (7S)-7-Amino-5,7-dihydro-6H-dibenzo[b,d]azepin-6-one

HRID 1374567Notes

Reaction equation

HRID 1374567 reaction equation
[NH2:1][C@@H:2]1[C:8](=[O:9])[N:7](CC2C=CC(OC)=CC=2)[C:6]2[CH:19]=[CH:20][CH:21]=[CH:22][C:5]=2[C:4]2[CH:23]=[CH:24][CH:25]=[CH:26][C:3]1=2.FC(F)(F)C(O)=O.FC(F)(F)S(O)(=O)=O>ClCCl>[NH2:1][C@@H:2]1[C:8](=[O:9])[NH:7][C:6]2[CH:19]=[CH:20][CH:21]=[CH:22][C:5]=2[C:4]2[CH:23]=[CH:24][CH:25]=[CH:26][C:3]1=2

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 62406Trifluoromethanesulfonic acidHCID 69037712(S)-7-amino-5-(4-methoxy-benzyl)-5H,7H-dibenzo[b,d]azepin-6-one

Product 1

HCID 25067537(7S)-7-Amino-5,7-dihydro-6H-dibenzo[b,d]azepin-6-oneYield 97.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 0.55 g (1.6 mmol) (S)-7-amino-5-(4-methoxy-benzyl)-5H,7H-dibenzo[b,d]azepin-6-one, 3.74 ml (50 mmol) trifluoroacetic acid and 1.4 ml (16 mmol) trifluormethane sulfonic acid in 38 ml dichloromethane was stirred at room temperature for 4 hours. The solvent was distilled off and extraction with aqueous sodium bicarbonate solution/ethyl acetate followed by chromatography on silicagel with ethylacetate/methanol (100-95/0-5) yielded 0.35 g (96%) (S)-7-amino-5H,7H-dibenzo[b,d]azepin-6-one as orange solid; MS: m/e: 225.4 (M+H+).

Workup

  1. distillationThe solvent was distilled off
  2. extractionextraction with aqueous sodium bicarbonate solution/ethyl acetate

Sources & evidence

ORD record
ord-9bf3202b43844610852c9d67408e26a0
Source dataset
uspto-grants-2007_01
Patent number
US07166587B2

Reaction notes

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