Water → HCID 66758880, compound

HRID 1166593Notes

Reaction equation

HRID 1166593 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2([OH:34])[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH:17]=[C:18]3[C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=4[C:22](=[O:29])[NH:21][C:20]4[CH:30]=[CH:31][CH:32]=[CH:33][C:19]3=4)[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.[H-].[Na+].[CH2:37](Br)[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1.O>CN(C=O)C.C(OCC)(=O)C>[CH2:37]([N:21]1[C:22](=[O:29])[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[C:18](=[CH:17][CH2:16][CH2:15][N:12]2[CH2:13][CH2:14][C:9]([C:6]3[CH:7]=[CH:8][C:3]([Cl:2])=[CH:4][CH:5]=3)([OH:34])[CH2:10][CH2:11]2)[C:19]2[CH:33]=[CH:32][CH:31]=[CH:30][C:20]1=2)[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1

Participants

7

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 66758579HCID 66758579, compound

Product 1

HCID 66758880HCID 66758880, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution 4-(4-chlorophenyl)-1-[3-(6,11-dihydro-6-oxo-5H-dibenz[b,e]azepin-11-ylidene)propyl]piperidin-4-ol hydrochloride (Example 39) (300 mg) in DMF (5 ml) were added sodium hydride (60% in oil, 200 mg), benzyl bromide (0.15 ml) and the mixture was stirred at room temperature for 1 hour. Water and ethyl acetate were added to the reaction mixture, the organic layer was separated and washed with saturated aqueous sodium chloride, and dried with magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography eluting with ethyl acetate to give the titled compound (180 mg).

Workup

  1. customthe organic layer was separated
  2. washwashed with saturated aqueous sodium chloride
  3. dry with materialdried with magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customThe residue was purified by silica gel chromatography
  6. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-4532e59e32a24b70a83a6432bc90e4e5
Source dataset
uspto-grants-2003_09
Patent number
US06613905B1

Reaction notes

Loading…