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

HRID 1177796Notes

Reaction equation

HRID 1177796 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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 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)+.

Workup

  1. customThe ice bath was removed
  2. concentrationThe reaction was concentrated
  3. custompartitioned between ethyl acetate and saturated sodium bicarbonate
  4. extractionThe aqueous 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

Sources & evidence

ORD record
ord-37eeb294f3864d56a59b2da9caacaa03
Source dataset
uspto-grants-2010_11
Patent number
US07842808B2

Reaction notes

Loading…