Tetrahydrofuran → HCID 10164978, compound

HRID 1359129Notes

Reaction equation

HRID 1359129 reaction equation
[NH2:1][CH2:2][CH:3]([C:11]1([OH:33])[CH2:16][CH2:15][N:14]([C:17]([C:19]2[CH:24]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:22]=[C:21]([C:29]([F:32])([F:31])[F:30])[CH:20]=2)=[O:18])[CH2:13][CH2:12]1)[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([Cl:10])[CH:5]=1.[O:34]1CCC[CH2:35]1>O>[F:31][C:29]([F:32])([F:30])[C:21]1[CH:20]=[C:19]([CH:24]=[C:23]([C:25]([F:26])([F:27])[F:28])[CH:22]=1)[C:17]([N:14]1[CH2:15][CH2:16][C:11]2([O:33][C:35](=[O:34])[NH:1][CH2:2][CH:3]2[C:4]2[CH:9]=[CH:8][CH:7]=[C:6]([Cl:10])[CH:5]=2)[CH2:12][CH2:13]1)=[O:18]

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 11352416HCID 11352416, compound

Product 1

HCID 10164978HCID 10164978, compoundYield 69.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 1.48 g (3 mmol) {4-[2-amino-1-(3-chloro-phenyl)-ethyl]-4-hydroxy-piperidin-1-yl}-(3,5-bis-trifluoromethyl-phenyl)-methanone in 30 ml of tetrahydrofuran 1.46 g (9 mmol)1,1′-carbonyl-diimidazole was added and the mixture was stirred over night at room temperature under argon. Water (15 ml) was added, the organic layer was separated, washed twice with a solution of hydrochloric acid (1 M), dried and evaporated. The residue was purified by flash column chromatography (SiO2, ethyl acetate) to yield 1.08 g (69%) of the title compound.

Workup

  1. customthe organic layer was separated
  2. washwashed twice with a solution of hydrochloric acid (1 M)
  3. customdried
  4. customevaporated
  5. customThe residue was purified by flash column chromatography (SiO2, ethyl acetate)

Sources & evidence

ORD record
ord-4870048254444bec9f5fbbca46343549
Source dataset
uspto-grants-2003_07
Patent number
US06599900B2

Reaction notes

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