Acetone → HCID 57655922, compound

HRID 911238Notes

Reaction equation

HRID 911238 reaction equation
[OH:1][C:2]1[C:12]2[CH2:11][CH2:10][N:9]([C:13](=[O:18])[C:14]([F:17])([F:16])[F:15])[CH2:8][CH2:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:25][C:26]([CH3:28])=O>>[CH2:28]([O:1][C:2]1[C:12]2[CH2:11][CH2:10][N:9]([C:13](=[O:18])[C:14]([F:17])([F:15])[F:16])[CH2:8][CH2:7][C:6]=2[CH:5]=[CH:4][CH:3]=1)[CH:26]=[CH2:25]

Participants

4

Reactant 3

HCID 180Acetone2×HCID 11430Potassium CarbonateHCID 22219609HCID 22219609, compound

Product 1

HCID 57655922HCID 57655922, compoundYield 98%

Procedure

Dissolve 6-hydroxy-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine (1 g, 3.9 mmol) in acetone (5 mL) and add powdered potassium carbonate (2.8 g, 20 mmol). Add dropwise a solution of alkyl bromide (1.04 mL, 12 mmol) in acetone (3 mL) over 10 min and stir at ambient temperature overnight. Filter solids, wash with acetone and concentrate in vacuo to give the desired intermediate as an off-white solid (1.15 g, 98%). GC-MS m/z: 299 (M+).

Workup

  1. filtrationFilter solids
  2. washwash with acetone
  3. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-db01cbe76ce942978057e0bc0d747c76
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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