Dichloromethane → 4-amino-N-(1-methylpiperidin-4-yl)-3-(trifluoromethoxy)benzamide

HRID 1914745Notes

Reaction equation

HRID 1914745 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[O:11][C:12]([F:15])([F:14])[F:13].ClCCl.CCN(C(C)C)C(C)C.[CH3:28][N:29]1[CH2:34][CH2:33][CH:32]([NH2:35])[CH2:31][CH2:30]1>>[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:35][CH:32]2[CH2:33][CH2:34][N:29]([CH3:28])[CH2:30][CH2:31]2)=[O:8])=[CH:4][C:3]=1[O:11][C:12]([F:15])([F:14])[F:13]

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 81531DiisopropylethylamineHCID 27359514-amino-3-(trifluoromethoxy)benzoic AcidHCID 27375314-Amino-1-methylpiperidine

Product 1

HCID 580151524-amino-N-(1-methylpiperidin-4-yl)-3-(trifluoromethoxy)benzamideYield 71%

Procedure

To a suspension of 4-amino-3-(trifluoromethoxy)benzoic acid (900 mg, 4 mmol) in dichloromethane (60 ml) TBTU (1.9 g, 6 mmol) and DIPEA (1.04 ml, 6 mmol) were added. The mixture was stirred at room temperature for 30 minutes. Then 1-methylpiperidin-4-amine (513 mg, 4.5 mmol) was added and the reaction was stirred for an additional 3 h. The solution was washed with water and the organic phase was dried over anhydrous Na2SO4. The crude was purified by flash chromatography (DCM/MeOH/NH3aq, 9:1:0.5), to give the title compound (900 mg, 71%), as an orange solid.

Workup

  1. additionwere added
  2. stirringthe reaction was stirred for an additional 3 h
  3. washThe solution was washed with water
  4. dry with materialthe organic phase was dried over anhydrous Na2SO4
  5. customThe crude was purified by flash chromatography (DCM/MeOH/NH3aq, 9:1:0.5)

Sources & evidence

ORD record
ord-3e5600baa2c8498ea0eb3752c04771d8
Source dataset
uspto-grants-2013_12
Patent number
US08614220B2

Reaction notes

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