Acetic Acid → 4-(2-Fluorobenzylthio)-4-(2-fluorophenyl)-1-methylpiperidine maleate

HRID 647539Notes

Reaction equation

HRID 647539 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1([OH:15])[CH2:13][CH2:12][N:11]([CH3:14])[CH2:10][CH2:9]1.[F:16][C:17]1[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=1[CH2:19][SH:20].B(F)(F)F.CC[O:31][CH2:32][CH3:33].[C:34]([OH:37])(=[O:36])[CH3:35]>>[C:32]([OH:31])(=[O:15])/[CH:33]=[CH:35]\[C:34]([OH:37])=[O:36].[F:16][C:17]1[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=1[CH2:19][S:20][C:8]1([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[F:1])[CH2:13][CH2:12][N:11]([CH3:14])[CH2:10][CH2:9]1

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 8000Boron trifluoride etherateHCID 5221752-Fluorobenzyl mercaptanHCID 126940234-(2-Fluorophenyl)-1-methylpiperidin-4-OL

Product 1

HCID 126940404-(2-Fluorobenzylthio)-4-(2-fluorophenyl)-1-methylpiperidine maleate

Procedure

A mixture of 4-(2-fluorophenyl)-4-hydroxy-1-methylpiperidine of Example 1a (15.8 g), 12 ml of 2-fluorobenzyl mercaptan and 20 ml of boron trifluoride etherate in 15 ml of glacial acetic acid is stirred at 65°-70° C. for 16 hours. The excess reagents are removed under reduced pressure, the residue is triturated with 300 ml of 0.5 N HCl and 100 ml of ether. After standing at 5°-10° C. for 30 minutes, a crystalline precipitate is filtered, air dried and made basic with 10% aqueous NH4OH. The liberated amine is taken up in either, dried and concentrated to a yellowish oil which is then converted to its maleate in ether, recrystallization of the crude salt from methanol-ether gives colorless prisms, m.p. 153°-154° C. of 4-(2-fluorobenzylthio)-4-(2-fluorophenyl)-1-methylpiperidine maleate.

Workup

  1. customThe excess reagents are removed under reduced pressure
  2. customthe residue is triturated with 300 ml of 0.5 N HCl and 100 ml of ether
  3. waitAfter standing at 5°-10° C. for 30 minutes
  4. filtrationa crystalline precipitate is filtered
  5. customair dried
  6. customdried
  7. concentrationconcentrated to a yellowish oil which
  8. customis then converted to its maleate in ether, recrystallization of the crude salt from methanol-ether

Sources & evidence

ORD record
ord-7692d3272a46457999d2faf423027815
Source dataset
uspto-grants-1983_10
Patent number
US04409229

Reaction notes

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