Water → HCID 18072498, compound

HRID 552138Notes

Reaction equation

HRID 552138 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:9]=[CH:8][CH:7]=[CH:6][C:4]=1[NH2:5].[C:12]([O:16][C:17]([N:19]1[CH2:24][CH2:23][CH:22]([C:25](Cl)=[O:26])[CH2:21][CH2:20]1)=[O:18])([CH3:15])([CH3:14])[CH3:13].C(N(CC)CC)C.O>ClCCl>[F:1][C:2]([F:10])([F:11])[C:3]1[CH:9]=[CH:8][CH:7]=[CH:6][C:4]=1[NH:5][C:25]([CH:22]1[CH2:23][CH2:24][NH:19][CH2:20][CH2:21]1)=[O:26].[C:12]([O:16][C:17]([N:19]1[CH2:24][CH2:23][CH:22]([C:25](=[O:26])[NH:5][C:4]2[CH:6]=[CH:7][CH:8]=[CH:9][C:3]=2[C:2]([F:10])([F:11])[F:1])[CH2:21][CH2:20]1)=[O:18])([CH3:15])([CH3:14])[CH3:13]

Participants

7

Reactant 4

HCID 962WaterHCID 69222-(Trifluoromethyl)anilineHCID 8471TriethylamineHCID 21906247HCID 21906247, compound

Product 2

HCID 18072498HCID 18072498, compoundHCID 67172280HCID 67172280, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2-(trifluoromethyl)aniline (0.5 mL, 4.20 mmol) in dichloromethane (10.0 mL) was added 4-chlorocarbonylpiperidine-1-carboxylic acid tert-butyl ester (1.000 g, 4.00 mmol). The reaction mixture was stirred at ambient temperature for 10 minutes, then followed by the addition of triethylamine (0.6 mL, 4.20 mmol). The reaction mixture was stirred at ambient temperature for another 10 minutes. Water (5.0 mL) was added to the mixture and the organic phase separated and washed with saturated NaCl (10 mL), dried over MgSO4 and then concentrated in vacuo. The obtained crude product was purified by column chromatography to yield the desired product, 4-(2-trifluoromethylphenylcarbamoyl)piperidine-1-carboxylic acid tert-butyl ester, in 30% yield (0.450 g). 1H NMR (300 MHz, CDCl3) δ 7.97 (d, J=8.0 Hz, 1H), 7.61 (s. 1H), 7.53 (d, J=7.9 Hz, 1H), 7.47 (t, J=7.5 Hz, 1H), 7.18 (t, J=7.6 Hz, 1H), 4.13-4.04 (m, 2H), 2.77-2.69 (m, 2H), 2.44-2.34 (m, 1H), 1.87-1.93 (m, 2H), 1.70-1.57 (m, 2H), 1.40 (s. 9H). MS (ES−) m/z 371 (M−1).

Workup

  1. stirringThe reaction mixture was stirred at ambient temperature for another 10 minutes
  2. customthe organic phase separated
  3. washwashed with saturated NaCl (10 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe obtained crude product
  7. customwas purified by column chromatography

Sources & evidence

ORD record
ord-ff6c4261fef64993ba2e187e5e37bb15
Source dataset
uspto-grants-2011_05
Patent number
US07951805B2

Reaction notes

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