Water → HCID 86586145, compound

HRID 430710Notes

Reaction equation

HRID 430710 reaction equation
[CH:1]1[C:11]2[CH:10]=[CH:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[CH:6]([C:16]#[N:17])[C:5]=2[CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Br[CH2:21][CH2:22][CH2:23][Cl:24].O>CN(C=O)C.C(OCC)(=O)C>[Cl:24][CH2:23][CH2:22][CH2:21][C:12]1[C:8]2[CH:9]=[CH:10][C:11]3[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=3[CH:6]([C:16]#[N:17])[C:7]=2[CH:15]=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 962WaterHCID 80061-Bromo-3-chloropropaneHCID 24758Sodium hydrideHCID 14950891HCID 14950891, compound

Product 1

HCID 86586145HCID 86586145, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5H-dibenzo[a,d]cycloheptene-5-carbonitrile (described in J. Med Chem. 1994, 37, 804-810) (500mg) in DMF (10 ml) were added 60% sodium hydride (110 mg) and 1-bromo-3- chloropropane (0.30 ml) and the mixture was stirred at room temperature for 1 hours. Water and ethyl acetate were added to the reaction mixture, the organic layer was separated and washed with saturated aqueous sodium chloride, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure to give 5-(3-chloropropyl-5H-dibenzo[a,d]cycloheptene-5-carbonitrile. Without purification, to a solution obtained chloride in DMF (10 ml) were added 4-(4-chlorophenyl)-4- hydroxypiperidine (650 mg), potassium carbonate (950 mg), and potassium iodide (50 mg) and the mixture was stirred at 70° C. for 24 hours. Water and ethyl acetate were added to the reaction mixture, the organic layer was separated and washed with saturated aqueous sodium chloride, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography eluting with ethyl acetate-hexane (1:1) to give the titled compound (700 mg). 1H-NMR (CDCl3) d: 1.22-1.34(2H,m), 1.60-1.80(3H,m), 1.93-1.99(2H,m), 2.16-2.28(6H,m), 2.56-2.60(2H,m), 6.98(2H,s), 7.25-7.47(10H,m), 8.00-8.03(2H,m). MS m/z: 469(M+1)

Workup

  1. customthe organic layer was separated
  2. washwashed with saturated aqueous sodium chloride
  3. dry with materialdried over magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-f9acf0d82a45497ba4e3bde8f96f09d9
Source dataset
uspto-grants-2001_11
Patent number
US06323206B1

Reaction notes

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