Chloroform → HCID 21488086, compound

HRID 1414583Notes

Reaction equation

HRID 1414583 reaction equation
[CH:1]1([C:4]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)([OH:10])[CH2:5][CH2:6][N:7]([CH3:9])[CH3:8])[CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].C(Cl)(Cl)[Cl:24].[C:27](Cl)(=[O:30])[CH2:28][CH3:29]>O>[ClH:24].[CH:1]1([C:4]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)([O:10][C:27](=[O:30])[CH2:28][CH3:29])[CH2:5][CH2:6][N:7]([CH3:8])[CH3:9])[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 6212Chloroform2×HCID 11430Potassium CarbonateHCID 62324Propionyl chlorideHCID 19816208HCID 19816208, compound

Product 1

HCID 21488086HCID 21488086, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A stirred mixture of 6 g. (0.027 mole) of 1-cyclopropyl-3-dimethylamino-1-phenyl-1-propanol and 20 g. (0.14 mole) of potassium carbonate in 25 ml. of chloroform was treated at 0° C. with 3 g. (0.032 mole) of freshly distilled propionyl chloride in 25 ml. of chloroform over a ten-minute period. The mixture was allowed to warm to room temperature and stirring was continued for 24 hours. The reaction mixture was treated with 50 ml. of water and stirring was continued another 30 minutes. The chloroform layer was separated, dried over magnesium sulfate and evaporated under reduced pressure to an oil. An ether solution of the oil was treated with ethereal hydrogen chloride. The salt was recrystallized from isopropanol-isopropyl ether mixture (yield was 4.2 g. (50%); m.p. 162°-164° C.). The analytical sample melted at 166°-168° C.

Workup

  1. additionA stirred mixture of 6 g
  2. additionThe reaction mixture was treated with 50 ml
  3. waitwas continued another 30 minutes
  4. customThe chloroform layer was separated
  5. dry with materialdried over magnesium sulfate
  6. customevaporated under reduced pressure to an oil
  7. additionAn ether solution of the oil was treated with ethereal hydrogen chloride
  8. customThe salt was recrystallized from isopropanol-isopropyl ether mixture (yield was 4.2 g. (50%); m.p. 162°-164° C.)

Sources & evidence

ORD record
ord-900a04ee2d11484a86678c7dfa23d80d
Source dataset
uspto-grants-1977_01
Patent number
US04001429

Reaction notes

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