Boron trifluoride etherate → 4-(4-Chlorobenzylthio)-4-(2-fluorophenyl)-1-methylpiperidine hydrochloride

HRID 647527노트

반응식

HRID 647527 반응식
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][SH:7])=[CH:4][CH:3]=1.B(F)(F)F.CCOCC.[F:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[C:26]1(O)[CH2:31][CH2:30][N:29]([CH3:32])[CH2:28][CH2:27]1>C(O)(=O)C>[ClH:1].[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][S:7][C:26]2([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=3[F:19])[CH2:31][CH2:30][N:29]([CH3:32])[CH2:28][CH2:27]2)=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 8000Boron trifluoride etherateHCID 804094-Chlorobenzyl mercaptanHCID 126940234-(2-Fluorophenyl)-1-methylpiperidin-4-OL

생성물 1

HCID 126940504-(4-Chlorobenzylthio)-4-(2-fluorophenyl)-1-methylpiperidine hydrochloride

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

9.9 ml (11.9 g) of 4-chlorobenzyl mercaptan and 11.1 ml of boron trifluoride etherate are added sequentially to 5.00 g of 4-(2-fluorophenyl)-4-hydroxy-1-methylpiperidine. Example 1a, in 11.1 ml of glacial acetic acid. The reaction is stirred at 55°-60° C. for 48 hours. The excess reagents are removed at 80° C. in vacuo and the residue is taken up with a 1:1 ether-2 N hydrochloride acid mixture. This biphasic mixture is stirred for 2.5 hours and then for an additional ten minutes after 50 ml of ice are added. The ether layer is decanted off. The aqueous layer is sequentially washed with ether and filtered to collect a crude product. The product is washed with a small portion of water and then a large portion of ether to give a white powder. The powder is recrystallized from acetone to give white crystals, mp 164°-166° C. of 4-(4-chlorobenzylthio)-4-(2-fluorophenyl)- 1-methylpiperidine hydrochloride.

후처리

  1. customThe excess reagents are removed at 80° C. in vacuo
  2. stirringThis biphasic mixture is stirred for 2.5 hours
  3. additionfor an additional ten minutes after 50 ml of ice are added
  4. customThe ether layer is decanted off
  5. washThe aqueous layer is sequentially washed with ether
  6. filtrationfiltered
  7. customto collect a crude product
  8. washThe product is washed with a small portion of water
  9. customa large portion of ether to give a white powder
  10. customThe powder is recrystallized from acetone

출처 및 근거

ORD 기록
ord-3764c175b370455b9300b62369181fb4
출처 데이터셋
uspto-grants-1983_10
특허 번호
US04409229

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