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

HRID 1248501ノート

反応式

HRID 1248501 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

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-2N 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.

後処理

  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

出典と根拠

ORDレコード
ord-c292458581b542518548cd0c5f018e76
出典データセット
uspto-grants-1985_06
特許番号
US04524207

反応ノート

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