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

HRID 1724667노트

반응식

HRID 1724667 반응식
[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

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acid2회HCID 9978463Tert-butyl 4-[3-fluoro(4-fluorobenzyl)anilino]-1-piperidinecarboxylate

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-dc4933c8a828413c9fe717a3d976430e
출처 데이터셋
uspto-grants-2009_02
특허 번호
US07488741B2

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