Thionyl Chloride → (R)-3-Chloro-1-(4-methoxyphenethyl)-3-methylpiperidine

HRID 1460483Notes

Reaction equation

HRID 1460483 reaction equation
S(Cl)([Cl:3])=O.O[CH2:6][C@:7]1([CH3:22])[CH2:11][CH2:10][CH2:9][N:8]1[CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1>ClCCl>[Cl:3][C@:7]1([CH3:22])[CH2:11][CH2:10][CH2:9][N:8]([CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[CH2:6]1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 53970712(S)-2-hydroxymethyl-1-(4-methoxyphenethyl)-2-methylpyrrolidine

Product 1

HCID 53871996(R)-3-Chloro-1-(4-methoxyphenethyl)-3-methylpiperidineYield 34.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Thionyl chloride (238 mg) was added slowly to a solution of (S)-2-hydroxymethyl-1-(4-methoxyphenethyl)-2-methylpyrrolidine (see Preparation 10) (349 mg) in dichloromethane (15 ml) and the mixture was heated under reflux for 2 hours. The reaction was cooled, diluted with dichloromethane, washed with 10% aqueous sodium carbonate solution, dried over sodium sulphate and evaporated under reduced pressure to give the title compound as a brown gum, (130 mg), which was characterised by NMR and used directly in Example 4 without further purification.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 hours
  3. temperatureThe reaction was cooled
  4. washwashed with 10% aqueous sodium carbonate solution
  5. dry with materialdried over sodium sulphate
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-e83732a689cc454192ef0c690c61c204
Source dataset
uspto-grants-1991_12
Patent number
US05071844

Reaction notes

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