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

HRID 1248512노트

반응식

HRID 1248512 반응식
[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

참가 물질

5

반응물 4

HCID 176Acetic AcidHCID 8000Boron trifluoride etherateHCID 522175(2-Fluorophenyl)methanethiolHCID 126940234-(2-Fluorophenyl)-1-methylpiperidin-4-OL

생성물 1

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

실험 절차

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 0.5N 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 ether, 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.

후처리

  1. customThe excess reagents are removed under reduced pressure
  2. customthe residue is triturated with 300 ml of 0.5N 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

출처 및 근거

ORD 기록
ord-3e3c249d726546f1be4b4dc3421cc9a2
출처 데이터셋
uspto-grants-1985_06
특허 번호
US04524207

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