Thionyl Chloride → HCID 12782362, compound

HRID 1863032Notes

Reaction equation

HRID 1863032 reaction equation
S(Cl)([Cl:3])=O.[ClH:5].O[CH:7]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[CH2:8][N:9]1[CH2:14][CH2:13][C:12]([N:18]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:19](=[O:22])[CH2:20][CH3:21])([CH2:15][O:16][CH3:17])[CH2:11][CH2:10]1>ClCCl>[ClH:3].[Cl:5][CH:7]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[CH2:8][N:9]1[CH2:14][CH2:13][C:12]([N:18]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:19](=[O:22])[CH2:20][CH3:21])([CH2:15][O:16][CH3:17])[CH2:11][CH2:10]1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 12298104HCID 12298104, compound

Product 1

HCID 12782362HCID 12782362, compoundYield 61.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 4.5 parts of sulfinyl chloride is added dropwise a mixture of 13 parts of N-[1-(2-hydroxy-2-phenylethyl)-4-(methoxymethyl)-4-piperidinyl]-N-phenylpropanamide hydrochloride and 260 parts of dichloromethane. Upon completion, the whole is stirred and refluxed for a few hours. The reaction mixture is cooled and the solvent is evaporated. The residue is taken up in 2-propanone. The mixture is filtered and the filtrate is treated with activated charcoal. The latter is filtered off and the filtrate is evaporated. The residue is crystallized from a mixture of 2-propanone and 2,2'-oxybispropane. The product is filtered off and dried, yielding 9.2 parts (61.7%) of N-[1-(2-chloro-2-phenylethyl)-4-(methoxymethyl)-4-piperidinyl]-N-phenylpropanamide monohydrochloride; mp. 145.3° C.

Workup

  1. temperaturerefluxed for a few hours
  2. temperatureThe reaction mixture is cooled
  3. customthe solvent is evaporated
  4. filtrationThe mixture is filtered
  5. additionthe filtrate is treated with activated charcoal
  6. filtrationThe latter is filtered off
  7. customthe filtrate is evaporated
  8. customThe residue is crystallized from a mixture of 2-propanone and 2,2'-oxybispropane
  9. filtrationThe product is filtered off
  10. customdried

Sources & evidence

ORD record
ord-d8ce5654b3ae4bceb72d5cf1ccc98cff
Source dataset
uspto-grants-1979_09
Patent number
US04167574

Reaction notes

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