Sodium Hydroxide → HCID 72187943, compound

HRID 515176Notes

Reaction equation

HRID 515176 reaction equation
C(O[C:4](=[O:22])[C:5]1[C:10]([C:11]([F:14])([F:13])[F:12])=[CH:9][C:8]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)=[CH:7][C:6]=1[CH3:21])C.[Cl:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28][NH2:29])=[CH:26][CH:25]=1.C[Al](C)C.[OH-].[Na+]>C1(C)C=CC=CC=1>[Cl:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28][NH:29][C:4](=[O:22])[C:5]2[C:10]([C:11]([F:12])([F:14])[F:13])=[CH:9][C:8]([N:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)=[CH:7][C:6]=2[CH3:21])=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 660364-ChlorobenzylamineHCID 16682925TrimethylaluminumHCID 86699744HCID 86699744, compound

Product 1

HCID 72187943HCID 72187943, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 2-methyl-4-morpholin-4-yl-6-(trifluoromethyl)-benzoic acid ethyl ester (0.27 g, 0.85 mmol), 4-chlorobenzylamine (1.21 g, 8.51 mmol) and trimethylaluminium (2M in toluene) (2.98 ml, 5.96 mmol) in toluene (9 ml) is heated at 110° C. for 4 d. After completion of the reaction (monitored by TLC), a 2M aqueous solution of sodium hydroxide is carefully added and the mixture is extracted with ethyl acetate (2×15 ml). The combined organic layers are washed with 2M aqueous solution of sodium hydroxide (10 ml), brine (10 ml) and dried over sodium sulfate. The solvent is evaporated to get the crude product, which is purified by column chromatography (silica gel, 30% ethyl acetate/cyclohexane) to afford N-[(4-chlorophenyl)-methyl]-2-methyl-4-morpholin-4-yl-6-(trifluoromethyl)-benzamide (example 19) (0.28 g, 0.68 mmol, 80%). [M+H]+ 413.1.

Workup

  1. customAfter completion of the reaction (monitored by TLC)
  2. extractionthe mixture is extracted with ethyl acetate (2×15 ml)
  3. washThe combined organic layers are washed with 2M aqueous solution of sodium hydroxide (10 ml), brine (10 ml)
  4. dry with materialdried over sodium sulfate
  5. customThe solvent is evaporated
  6. customto get the crude product, which
  7. customis purified by column chromatography (silica gel, 30% ethyl acetate/cyclohexane)

Sources & evidence

ORD record
ord-b0956bcf522e4bbab6fad6dff995ac3f
Source dataset
uspto-grants-2015_08
Patent number
US09108936B2

Reaction notes

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