Trifluoroacetic acid → 2-Amino-N-(1-benzylpiperidin-4-yl)-3-fluorobenzamide

HRID 2099729노트

반응식

HRID 2099729 반응식
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[C:18]=2[NH:24]C(=O)OC(C)(C)C)=[O:16])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>ClCCl>[NH2:24][C:18]1[C:19]([F:23])=[CH:20][CH:21]=[CH:22][C:17]=1[C:15]([NH:14][CH:11]1[CH2:12][CH2:13][N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:9][CH2:10]1)=[O:16]

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 59639684tert-Butyl 2-(1-benzylpiperidin-4-ylcarbamoyl)-6-fluorophenylcarbamate

생성물 1

HCID 211021192-Amino-N-(1-benzylpiperidin-4-yl)-3-fluorobenzamide

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of tert-butyl 2-(1-benzylpiperidin-4-ylcarbamoyl)-6-fluorophenylcarbamate (67.0 g, 157 mmol) in dichloromethane (700 mL) at 0° C. was added trifluoroacetic acid (100 mL). The ice bath was removed and the reaction stirred at room temperature overnight. The reaction was concentrated and partitioned between ethyl acetate and saturated sodium bicarbonate. The aqueous portion was extracted with ethyl acetate (2×), which were washed with water (3×), then brine, dried over magnesium sulfate, and concentrated to give 47.6 g (93%) as a white solid which was used without purification. Mass spec.: 328.33 (MH)+.

후처리

  1. customThe ice bath was removed
  2. concentrationThe reaction was concentrated
  3. custompartitioned between ethyl acetate and saturated sodium bicarbonate
  4. extractionThe aqueous portion was extracted with ethyl acetate (2×), which
  5. washwere washed with water (3×)
  6. dry with materialbrine, dried over magnesium sulfate
  7. concentrationconcentrated
  8. customto give 47.6 g (93%) as a white solid which
  9. customwas used without purification

출처 및 근거

ORD 기록
ord-b8fbe27ca41b4cff86abe6bac1158d65
출처 데이터셋
uspto-grants-2009_08
특허 번호
US07569578B2

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