Acetic Acid → HCID 12694032, compound

HRID 647534Notes

Reaction equation

HRID 647534 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]1([OH:16])[CH2:14][CH2:13][N:12]([CH3:15])[CH2:11][CH2:10]1.B(F)(F)F.CC[O:23][CH2:24][CH3:25].[CH2:26]([SH:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.[C:34]([OH:37])(=[O:36])[CH3:35]>>[C:24]([OH:23])(=[O:16])/[CH:25]=[CH:35]\[C:34]([OH:37])=[O:36].[CH2:26]([S:33][C:9]1([C:3]2[CH:4]=[C:5]([F:8])[CH:6]=[CH:7][C:2]=2[F:1])[CH2:14][CH2:13][N:12]([CH3:15])[CH2:11][CH2:10]1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 7509Benzyl mercaptanHCID 8000Boron trifluoride etherateHCID 12694024HCID 12694024, compound

Product 1

HCID 12694032HCID 12694032, compound

Conditions

Temperature
65 °C

Procedure

A mixture of 4-(2,5-difluorophenyl)-4-hydroxy-1-methyl-piperidine, free base of a, 4 ml of boron trifluoride etherate, 5 ml of benzyl mercaptan and 5 ml of glacial acetic acid is stirred at 65° C. for 16 hours. Excess acid is removed under reduced pressure with the residue equilibrated with 0.5 N hydrochloric acid and ether and the resulting solution is stirred at 10°-20° C. for four hours. The resulting crystalline precipitate is sequentially collected by filtration, basified and extracted with ether providing the desired product as an oil. The oil is converted to its maleic acid salt which is recrystallized from an acetone-ether mixture to provide prisms, m.p. 164°-166° C. of 4-benzylthio-4-(2,5-difluorophenyl)-1-methylpiperidine maleate.

Workup

  1. customExcess acid is removed under reduced pressure with the residue
  2. stirringthe resulting solution is stirred at 10°-20° C. for four hours
  3. filtrationThe resulting crystalline precipitate is sequentially collected by filtration
  4. extractionextracted with ether providing the desired product as an oil
  5. customis recrystallized from an acetone-ether mixture

Sources & evidence

ORD record
ord-a62822f5312643fba79358080a4b54af
Source dataset
uspto-grants-1983_10
Patent number
US04409229

Reaction notes

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