Dichloromethane → 4-(4-Trifluoromethylphenylamino)piperidine-1-carbonylchloride

HRID 856140Notes

Reaction equation

HRID 856140 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:8]=[CH:7][C:6]([NH:9]N2CCCCC2)=[CH:5][CH:4]=1.[Cl:18][C:19](Cl)([O:21]C(=O)OC(Cl)(Cl)Cl)Cl.C([N:32]([CH2:35][CH3:36])[CH2:33][CH3:34])C.[CH2:37](Cl)Cl>>[F:17][C:2]([F:1])([F:16])[C:3]1[CH:4]=[CH:5][C:6]([NH:9][CH:37]2[CH2:34][CH2:33][N:32]([C:19]([Cl:18])=[O:21])[CH2:35][CH2:36]2)=[CH:7][CH:8]=1

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 94429TriphosgeneHCID 23081449(4-Trifluoromethylphenylamino)piperidine

Product 1

HCID 230810884-(4-Trifluoromethylphenylamino)piperidine-1-carbonylchloride

Procedure

A mixture of (4-trifluoromethylphenylamino)-piperidine (1.14 g, 4.67 mmol), triphosgene (0.55 g, 1.87 mmol), and triethylamine (0.98 ml, 7.01 mmol) in methylene chloride (10 ml) was stirred at room temperature for 1.5 hours. The reaction mixture was washed with water, and dried over magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure to afford 4-(4-trifluoromethylphenylamino)piperidine-1-carbonylchloride (1.43 g, quantitative) as a pale yellow oil.

Workup

  1. washThe reaction mixture was washed with water
  2. dry with materialdried over magnesium sulfate
  3. filtrationAfter filtration
  4. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-294c295f681641c0bb6a5b434c65f72b
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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