Acetyl chloride → Nexeridine

HRID 1283131Notes

Reaction equation

HRID 1283131 reaction equation
[CH3:1][N:2]([CH3:19])[CH2:3][CH:4]([C:6]1([OH:18])[CH2:11][CH2:10][CH2:9][CH2:8][CH:7]1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH3:5].[C:20](Cl)(=[O:22])[CH3:21]>C(Cl)(Cl)Cl>[C:20]([O:18][C:6]1([CH:4]([CH3:5])[CH2:3][N:2]([CH3:1])[CH3:19])[CH2:11][CH2:10][CH2:9][CH2:8][CH:7]1[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)(=[O:22])[CH3:21]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 21519258HCID 21519258, compound

Product 1

HCID 10447719Nexeridine

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

(-)-1-(2-Dimethylamino-1-methylethyl)-2-phenycyclohexanol (8 gm) in 65 ml chloroform is cooled to 0° and 2.7 ml acetyl chloride is added at ≤5°. After warming to room temperature, the solution is extracted with dilute aqueous sodium hydroxide, washed with water and dried over magnesium sulfate. The dried chloroform solution is then cooled to 0° and treated with another 3.0 ml acetyl chloride at ≤5° and again allowed to warm to room temperature, extracted with dilute sodium hydroxide, washed with water and dried over magnesium sulfate. Removal of solvent leaves 9.3 gm of an oil which crystallizes spontaneously. This is recrystallized from 30 ml n-hexane (at -50°) yielding 5.7 gm product melting at 63°-66°. The optical rotation is as follows: ##EQU8##

Workup

  1. extractionthe solution is extracted with dilute aqueous sodium hydroxide
  2. washwashed with water
  3. dry with materialdried over magnesium sulfate
  4. temperatureThe dried chloroform solution is then cooled to 0°
  5. additiontreated with another 3.0 ml acetyl chloride at ≤5°
  6. temperatureto warm to room temperature
  7. extractionextracted with dilute sodium hydroxide
  8. washwashed with water
  9. dry with materialdried over magnesium sulfate
  10. customRemoval of solvent

Sources & evidence

ORD record
ord-5ed0dab380d14a2a8d6ce97351bfa6a2
Source dataset
uspto-grants-1976_08
Patent number
US03974157

Reaction notes

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