Sodium hydride → 8-(3,5-Bis-trifluoromethyl-benzoyl)-3-(2-morpholin-4-yl-ethyl)-1-phenyl-1,3,8-triaza-spiro[4.5]decan-4-one

HRID 1018549Notes

Reaction equation

HRID 1018549 reaction equation
[H-].[Na+].[F:3][C:4]([F:35])([F:34])[C:5]1[CH:6]=[C:7]([CH:27]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:29]=1)[C:8]([N:10]1[CH2:26][CH2:25][C:13]2([N:17]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:16][NH:15][C:14]2=[O:24])[CH2:12][CH2:11]1)=[O:9].Cl.Cl[CH2:38][CH2:39][N:40]1[CH2:45][CH2:44][O:43][CH2:42][CH2:41]1.C(=O)(O)[O-].[Na+]>CN1CCCC1=O>[F:35][C:4]([F:3])([F:34])[C:5]1[CH:6]=[C:7]([CH:27]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:29]=1)[C:8]([N:10]1[CH2:11][CH2:12][C:13]2([N:17]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH2:16][N:15]([CH2:38][CH2:39][N:40]3[CH2:45][CH2:44][O:43][CH2:42][CH2:41]3)[C:14]2=[O:24])[CH2:25][CH2:26]1)=[O:9]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)HCID 516892Sodium BicarbonateHCID 184017258-(3,5-Bis-trifluoromethyl-benzoyl)-1-phenyl-1,3,8-triaza-spiro[4.5]decan-4-one

Product 1

HCID 184017158-(3,5-Bis-trifluoromethyl-benzoyl)-3-(2-morpholin-4-yl-ethyl)-1-phenyl-1,3,8-triaza-spiro[4.5]decan-4-oneYield 73%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
100 °C

Procedure

Sodium hydride (34 mg, 60%) was suspended in N-methyl-2-pyrrolidone (2 mL) and 8-(3,5-bis-trifluoromethyl-benzoyl)-1-phenyl-1,3,8-triaza-spiro[4.5]decan-4-one (200 mg) was added with stirring. After 5 minutes stirring at room temperature 4-(2-chloroethyl)morpholine hydrochloride (79 mg) was added. The mixture was heated to 100° C. with stirring and kept for 1 h at that temperature. After cooling, saturated sodium bicarbonate solution was added and the mixture was extracted with ethylacetate. Organic phases were pooled, dried with Na2SO4 and the solvent was evaporated. Chromatography on silica gel (ethylacetate) yielded the desired product (180 mg, 73%), MS: m/e=585.1 (M+H+).

Workup

  1. additionwas added
  2. stirringwith stirring
  3. temperatureAfter cooling
  4. extractionthe mixture was extracted with ethylacetate
  5. dry with materialdried with Na2SO4
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-3409937d13da4c4fb966863c3f6b1835
Source dataset
uspto-grants-2002_11
Patent number
US06482829B2

Reaction notes

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