Water → HCID 53724730, compound

HRID 430712Notes

Reaction equation

HRID 430712 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([OH:44])[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][CH:17]([CH:29]3[C:35]4[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=4[CH2:33][S:32][C:31]4[CH:40]=[CH:41][CH:42]=[CH:43][C:30]3=4)[CH2:18][NH:19][C:20](=O)OC3C=CC=CC=3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[NH2:45][CH2:46][CH2:47][CH2:48][OH:49].C(=O)([O-])[O-].[K+].[K+].[OH2:56]>CN(C=O)C.C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([OH:44])[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][CH:17]([CH:29]3[C:35]4[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=4[CH2:33][S:32][C:31]4[CH:40]=[CH:41][CH:42]=[CH:43][C:30]3=4)[CH2:18][NH:19][C:20]([NH:45][CH2:46][CH2:47][CH2:48][OH:49])=[O:56])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 90863-Amino-1-propanolHCID 11430Potassium CarbonateHCID 18462016HCID 18462016, compound

Product 1

HCID 53724730HCID 53724730, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution phenyl N-[2-[3-[4-(4-chlorophenyl)-4-hydroxypiperidino]propyl]-2-(6,11-dihydrodibenzo[b,e]thiepin-11-yl)ethyl]carbamate (300 mg) in DMF (10 ml) were added 3-amino-1-propanol (70 mg), potassium carbonate (130 mg) and the mixture was stirred at room temperature for 16 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-methanol (9:1) to give the titled compound (200 mg). 1H-NMR (CDCl3) d: 1.40-1.70(6H,m), 2.01-2.08(2H,m), 2.30-2.63(8H,m), 3.12 (2H,q), 3.42(2H,t), 4.00-4.12(2H,m), 4.22-4.28(2H,m), 4.82(1H,brt), 4.99(1H,brs), 6.98-7.45(12H,m).MS m/z: 594(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
  5. customThe residue was purified by silica gel chromatography
  6. washeluting with ethyl acetate-methanol (9:1)

Sources & evidence

ORD record
ord-6908e9b9c1b44c8287ff29b55e44fb7e
Source dataset
uspto-grants-2001_11
Patent number
US06323206B1

Reaction notes

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