Triphenylphosphine → 4-[2,2,2-Trifluoro-1-(2-piperidin-1-yl-ethoxy)-1-trifluoromethyl-ethyl]-phenylamine

HRID 557379Notes

Reaction equation

HRID 557379 reaction equation
CCOC(/N=N/C(O[CH2:11][CH3:12])=O)=O.[NH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]([OH:29])([C:25]([F:28])([F:27])[F:26])[C:21]([F:24])([F:23])[F:22])=[CH:16][CH:15]=1.[NH:30]1[CH2:35][CH2:34][CH2:33][CH2:32][CH:31]1C(O)C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C1COCC1>[F:28][C:25]([F:26])([F:27])[C:20]([C:17]1[CH:16]=[CH:15][C:14]([NH2:13])=[CH:19][CH:18]=1)([O:29][CH2:34][CH2:35][N:30]1[CH2:12][CH2:11][CH2:33][CH2:32][CH2:31]1)[C:21]([F:22])([F:23])[F:24]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 3356821-(Piperidin-2-yl)ethan-1-olHCID 5778012-(4-Aminophenyl)-1,1,1,3,3,3-hexafluoropropan-2-olHCID 5462977Diethyl azodicarboxylate

Product 1

HCID 222493264-[2,2,2-Trifluoro-1-(2-piperidin-1-yl-ethoxy)-1-trifluoromethyl-ethyl]-phenylamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

DEAD (366 mg, 2.1 mmol) was added drop-wise to the solution of 2-(4-aminophenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol (520 mg, 2 mmol), 2-piperidylethan-1-ol (260 mg, 2 mmol) and PPh3 (550 mg, 2.1 mmol) in THF (10 mL). The mixture was stirred for 2 h. The reaction was partitioned between EtOAc and aqueous NaHCO3 solution and the organic phase was washed with brine. After concentrated in vacuo, the organic residue was purified by flash chromatography on silica to give the title intermediate.

Workup

  1. customThe reaction was partitioned between EtOAc and aqueous NaHCO3 solution
  2. washthe organic phase was washed with brine
  3. concentrationAfter concentrated in vacuo
  4. customthe organic residue was purified by flash chromatography on silica

Sources & evidence

ORD record
ord-edbbdc3ccb47424788873680dd2553e3
Source dataset
uspto-grants-2011_11
Patent number
US08058445B2

Reaction notes

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