Water → 8-(3,5-Bis-trifluoromethyl-benzoyl)-1-phenyl-1,3,8-triaza-spiro[4.5]decan-4-one

HRID 1018546Notes

Reaction equation

HRID 1018546 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:11]=1)[C:6](Cl)=[O:7].[C:18]1([N:24]2[C:28]3([CH2:33][CH2:32][NH:31][CH2:30][CH2:29]3)[C:27](=[O:34])[NH:26][CH2:25]2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(N(CC)CC)C.O>ClCCl>[F:1][C:2]([F:17])([F:16])[C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:11]=1)[C:6]([N:31]1[CH2:30][CH2:29][C:28]2([N:24]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:25][NH:26][C:27]2=[O:34])[CH2:33][CH2:32]1)=[O:7]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 705561-Phenyl-1,3,8-triazaspiro(4.5)decan-4-oneHCID 1018563,5-Bis(trifluoromethyl)benzoyl chloride

Product 1

HCID 184017258-(3,5-Bis-trifluoromethyl-benzoyl)-1-phenyl-1,3,8-triaza-spiro[4.5]decan-4-oneYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 3,5-bis(trifluoromethyl)benzoyl chloride (2.3 mL, 13 mmol) in dichloromethane (50 mL) was added with stirring to a mixture of 1-phenyl-1,3,8-triaza-spiro[4.5]decan-4-one (2.9 g, 13 mmol) and triethylamine (3.5 mL, 25 mmol) in dichloromethane (250 mL) at room temperature. Stirring was continued for 2 h. Water (150 mL) was added, the phases were separated and the water phase was extracted twice with dichloromethane (100 mL). Organic phases were pooled, washed with brine (200 mL), dried with Na2SO4 and the solvent was evaporated. Chromatography on silica gel (ethylacetate/n-hexane 1:1) yielded the desired product (5.3 g, 89%) m.p. 251° C. and MS: m/e=472.1 (M+H+).

Workup

  1. customthe phases were separated
  2. extractionthe water phase was extracted twice with dichloromethane (100 mL)
  3. washwashed with brine (200 mL)
  4. dry with materialdried with Na2SO4
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-b22e33890aed453aa641b4594935371d
Source dataset
uspto-grants-2002_11
Patent number
US06482829B2

Reaction notes

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