Water → HCID 57263458, compound

HRID 1033328Notes

Reaction equation

HRID 1033328 reaction equation
C(N(CC)CC)C.[C:8](Cl)(=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[CH2:17]([C@@H:24]1[CH2:29][C@@H:28]([N:30]([CH2:37][C:38]2[C:47]3[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=3)[N:41]=[CH:40][CH:39]=2)[C:31](=[O:36])[C:32]([F:35])([F:34])[F:33])[CH2:27][CH2:26][NH:25]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.O>C(Cl)Cl>[CH2:17]([C@@H:24]1[CH2:29][C@@H:28]([N:30]([CH2:37][C:38]2[C:47]3[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=3)[N:41]=[CH:40][CH:39]=2)[C:31](=[O:36])[C:32]([F:34])([F:35])[F:33])[CH2:27][CH2:26][N:25]1[C:8](=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 57202094(2R*,4S*)-2-Benzyl-N-(4-quinolylmethyl)-N-trifluoroacetyl-4-piperidinamine

Product 1

HCID 57263458HCID 57263458, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

72 μl (0.515 mmol) of triethylamine and 54 μl (0.468 mmol) of benzoyl chloride are added to a solution of 200 mg (0.468 mmol) of (2R*,4S*)-2-benzyl-N-(4-quinolylmethyl)-N-trifluoroacetyl-4-piperidinamine in 4 ml of methylene chloride. The reaction mixture is stirred at 0° for 3 hours, water is added, extraction with methylene chloride is carried out. The organic phases are dried over magnesium sulfate and evaporated to dryness. The yellow oil is chromatographed on silica gel with methylene chloride/methanol/conc. ammonia (1000:50:1). The title compound is obtained as white foam. TLC: methylene chloride/methanol/conc. ammonia (700:50:1) Rf =0.72, FD-MS: M+ =531.

Workup

  1. extractionextraction with methylene chloride
  2. dry with materialThe organic phases are dried over magnesium sulfate
  3. customevaporated to dryness
  4. customThe yellow oil is chromatographed on silica gel with methylene chloride/methanol/conc

Sources & evidence

ORD record
ord-5f98b5f186e040bd8c6555f2856f8ff6
Source dataset
uspto-grants-1994_05
Patent number
US05310743

Reaction notes

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