2-Bromopropane → N-Trifluoroacetyl-8-bromo-7-isopropoxy-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine

HRID 2389413Notes

Reaction equation

HRID 2389413 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]([N:5]1[CH2:11][CH:10]([CH3:12])[C:9]2[CH:13]=[C:14]([Br:18])[C:15]([OH:17])=[CH:16][C:8]=2[CH2:7][CH2:6]1)=[O:4].[CH:21](Br)([CH3:23])[CH3:22].C1CCN2C(=NCCC2)CC1>ClCCl.CCOC(C)=O>[F:20][C:2]([F:19])([F:1])[C:3]([N:5]1[CH2:11][CH:10]([CH3:12])[C:9]2[CH:13]=[C:14]([Br:18])[C:15]([O:17][CH:21]([CH3:23])[CH3:22])=[CH:16][C:8]=2[CH2:7][CH2:6]1)=[O:4]

Participants

6

Reactant 3

HCID 63582-BromopropaneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 22292819N-Trifluoroacetyl-8-bromo-7-hydroxy-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine

Product 1

HCID 22292803N-Trifluoroacetyl-8-bromo-7-isopropoxy-methyl-2,3,4,5-tetrahydro-1H-3-benzazepineYield 35.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of N-trifluoroacetyl-8-bromo-7-hydroxy-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine (0.035 g, 0.099 mmol) in dichloromethane (1 mL) was treated with isopropyl bromide (0.037 g, 0.297 mmol), DBU (0.048 g, 0.205 mmol) and stirred 2 hours at 20 C. The product mixture was diluted with EtOAc (10 mL), washed with 5% aqueous HCl (5 mL), brine (5 mL), dried with Na2SO4 and concentrated. Flash chromatography (15% EtOAc in hexane, silica) resulted in 0.014 g of a clear oil. MS calculated for C16H19BrF3NO2+H: 394, observed: 394.

Workup

  1. washwashed with 5% aqueous HCl (5 mL), brine (5 mL)
  2. dry with materialdried with Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-b0cff9d67ada4119b4dbae4167d2c9fa
Source dataset
uspto-grants-2012_09
Patent number
US08273734B1

Reaction notes

Loading…