Trifluoroacetic acid → N-(4-fluorobenzyl)-N-(3-fluorophenyl)-4-piperidinamine

HRID 1724667ノート

反応式

HRID 1724667 の反応式
[F:1][C:2]1[CH:3]=[C:4]([CH:27]=[CH:28][CH:29]=1)[N:5]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=1)[CH:6]1[CH2:11][CH2:10][N:9](C(OC(C)(C)C)=O)[CH2:8][CH2:7]1.C(O)(C(F)(F)F)=O>ClCCl>[F:26][C:23]1[CH:22]=[CH:21][C:20]([CH2:19][N:5]([C:4]2[CH:27]=[CH:28][CH:29]=[C:2]([F:1])[CH:3]=2)[CH:6]2[CH2:7][CH2:8][NH:9][CH2:10][CH2:11]2)=[CH:25][CH:24]=1

参加物

4

反応物 2

HCID 6422Trifluoroacetic acid2 回HCID 9978463Tert-butyl 4-[3-fluoro(4-fluorobenzyl)anilino]-1-piperidinecarboxylate

生成物 1

HCID 9882852N-(4-fluorobenzyl)-N-(3-fluorophenyl)-4-piperidinamine収率 96%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

Tert-butyl 4-[3-fluoro(4-fluorobenzyl)anilino]-1-piperidinecarboxylate 8 (25.5 g) was dissolved in dichloromethane and the solution was cooled to 0° C. TFA (30 ml) was added to the solution and the reaction mixture was stirred at room temperature. After 1 h 30, TFA (20 ml) was added and the reaction mixture was stirred for a further 30 minutes. The solvent was removed under vacuum and the residue was taken up in dichloromethane and water. The aqueous phase was alkalized by addition of NaOH and washed with dichloromethane. The combined organic layers were dried over MgSO4 and concentrated. The crude was purified by chromatography (eluant: CH2Cl2/MeOH/NH4OH 95/5/0.5) to give N-(4-fluorobenzyl)-N-(3-fluorophenyl)-4-piperidinamine (18.4 g) as a free base.

後処理

  1. stirringthe reaction mixture was stirred for a further 30 minutes
  2. customThe solvent was removed under vacuum
  3. additionThe aqueous phase was alkalized by addition of NaOH
  4. washwashed with dichloromethane
  5. dry with materialThe combined organic layers were dried over MgSO4
  6. concentrationconcentrated
  7. customThe crude was purified by chromatography (eluant: CH2Cl2/MeOH/NH4OH 95/5/0.5)

出典と根拠

ORDレコード
ord-dc4933c8a828413c9fe717a3d976430e
出典データセット
uspto-grants-2009_02
特許番号
US07488741B2

反応ノート

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