Water → HCID 178482766, compound

HRID 2209806Notes

Reaction equation

HRID 2209806 reaction equation
[Cl:1][C:2]1[CH:26]=[CH:25][C:5]([C:6]([N:8]([C@H:10]2[CH2:15][CH2:14][C@H:13]([C:16]3[CH:21]=[CH:20][C:19](CNC)=[CH:18][CH:17]=3)[CH2:12][CH2:11]2)[CH3:9])=[O:7])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:34][CH2:35][CH2:36][OH:37].O.[CH3:39][N:40](C)[CH:41]=O>>[Cl:1][C:2]1[CH:26]=[CH:25][C:5]([C:6]([N:8]([C@H:10]2[CH2:11][CH2:12][C@H:13]([C:16]3[CH:17]=[CH:18][C:19]([CH2:34][CH2:35][CH2:36][OH:37])=[CH:20][C:21]=3[CH2:39][NH:40][CH3:41])[CH2:14][CH2:15]2)[CH3:9])=[O:7])=[CH:4][CH:3]=1

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 123083-Bromo-1-propanolHCID 178482784HCID 178482784, compound

Product 1

HCID 178482766HCID 178482766, compound

Procedure

5.0 g (0,013 Mol) of trans-N-(4-chlorobenzoyl)-N-methyl-4-(4-methylaminomethylphenyl)cyclohexylamine, 2.1 g (0.0148 Mol) of potassium carbonate and 2.1 g (0.015 mol) of 3-bromo-1-propanol are stirred together in 30 ml of dimethylformamide at ambient temperature for 40 hours. Then the reaction mixture is poured into water and extracted with ethyl acetate. After washing with water and saturated saline solution the mixture is evaporated down and the residue is purified by column chromatography (aluminium oxide, ethyl acetate/methanol=70:1 to 40:1, v:v). 3.8 g (68% of theory) of the title compound are obtained, melting point 98°-100° C. 1H-NMR spectrum (200 MHz, CDCl3); signals at ppm: 1.35 (m, 1H) , 1.6-2.1 (m, 9H) , 2.2 (2s, 3H) , 2.35-2.55 (m, 1H), 2.6 (t,2H), 2.8-3.1 (m,3H), 3.45 (s,2H), 3.75 (t,2H), 3.6+4.6 (t+m, 1H), 7.0-7.5 (m,8H).

Workup

  1. extractionextracted with ethyl acetate
  2. washAfter washing with water and saturated saline solution the mixture
  3. customis evaporated down
  4. customthe residue is purified by column chromatography (aluminium oxide, ethyl acetate/methanol=70:1 to 40:1, v:v)

Sources & evidence

ORD record
ord-91309e56b71945afb1cff84d5611e273
Source dataset
uspto-grants-1995_10
Patent number
US05455273

Reaction notes

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