Water → HCID 21519282, compound

HRID 1283140Notes

Reaction equation

HRID 1283140 reaction equation
[CH3:1][N:2]([CH3:20])[CH2:3][CH:4]([C:6]1([OH:19])[CH2:11][CH2:10][CH2:9][CH2:8][CH:7]1[C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1)[CH3:5].[CH2:21]([Cl:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[ClH:28].[CH2:21]([O:18][C:15]1[CH:14]=[CH:13][C:12]([CH:7]2[CH2:8][CH2:9][CH2:10][CH2:11][C:6]2([CH:4]([CH3:5])[CH2:3][N:2]([CH3:1])[CH3:20])[OH:19])=[CH:17][CH:16]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 21519227HCID 21519227, compound

Product 1

HCID 21519282HCID 21519282, compoundYield 69.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-(2-Dimethylamino-1-methylethyl)-2-(p-hydroxyphenyl)-cyclohexanol (Example XXX) (5.6 g) in 50 ml dimethylformamide is treated with 3.8 g benzyl chloride and 6 g potassium carbonate and stirred 3 hours at 90°. The mixture is cooled, 200 ml water added and extracted with 7×50 ml ethyl acetate. The extract is washed with water, dried and concentrated. The residue is dissolved in 65 ml ethyl acetate and acidified with HCl gas to give 5.7 g product, m. 253°-4°.

Workup

  1. temperatureThe mixture is cooled
  2. extractionextracted with 7×50 ml ethyl acetate
  3. washThe extract is washed with water
  4. customdried
  5. concentrationconcentrated
  6. dissolutionThe residue is dissolved in 65 ml ethyl acetate

Sources & evidence

ORD record
ord-4149b2c9c3ed4be5a58e047bb851c847
Source dataset
uspto-grants-1976_08
Patent number
US03974157

Reaction notes

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