Benzyl Bromide → 1-(7-Benzyloxy-8-nitro-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-2,2,2-trifluoro-ethanone

HRID 2174712Notes

Reaction equation

HRID 2174712 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]([N:5]1[CH2:11][CH2:10][C:9]2[CH:12]=[C:13]([OH:19])[C:14]([N+:16]([O-:18])=[O:17])=[CH:15][C:8]=2[CH2:7][CH2:6]1)=[O:4].C(=O)([O-])[O-].[K+].[K+].[CH2:28](Br)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>CN(C=O)C>[CH2:28]([O:19][C:13]1[C:14]([N+:16]([O-:18])=[O:17])=[CH:15][C:8]2[CH2:7][CH2:6][N:5]([C:3](=[O:4])[C:2]([F:1])([F:20])[F:21])[CH2:11][CH2:10][C:9]=2[CH:12]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 857522192,2,2-Trifluoro-1-(7-hydroxy-8-nitro-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-ethanone

Product 1

HCID 866445601-(7-Benzyloxy-8-nitro-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-2,2,2-trifluoro-ethanone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.30 g (4.27 mmol) 2,2,2-trifluoro-1-(7-hydroxy-8-nitro-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-ethanone are placed in 20 ml DMF and at room temperature 0.65 g (4.70 mmol) potassium carbonate and 0.508 ml (4.27 mmol) benzylbromide are added and the mixture is stirred for 3 h. Then it is filtered and the filtrate is concentrated by evaporation i.vac., the residue is triturated with water, suction filtered and dried at 45° C. in the circulating air dryer.

Workup

  1. additionare added
  2. filtrationThen it is filtered
  3. concentrationthe filtrate is concentrated by evaporation i.vac
  4. custom, the residue is triturated with water, suction
  5. filtrationfiltered
  6. customdried at 45° C. in the circulating air dryer

Sources & evidence

ORD record
ord-46642f0594a4463a9a9dc58df2246e29
Source dataset
uspto-grants-2015_06
Patent number
US09062034B2

Reaction notes

Loading…