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Sodium Hydroxide → 1h-Indole-7-carboxamide,n-[[4-(1,1-dimethylethyl)phenyl]methyl]-2,3-dihydro-n-(2-phenylethyl)-

HRID 855425
Notes
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Reaction equation

HRID 855425 reaction equation
[C:1]([C:5]1[CH:31]=[CH:30][C:8]([CH2:9][N:10]([CH2:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:11]([C:13]2[CH:14]=[CH:15][CH:16]=[C:17]3[C:21]=2[NH:20][CH:19]=[CH:18]3)=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C([BH3-])#N.[Na+].[OH-].[Na+]>C(O)(=O)C>[C:1]([C:5]1[CH:31]=[CH:30][C:8]([CH2:9][N:10]([CH2:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:11]([C:13]2[CH:14]=[CH:15][CH:16]=[C:17]3[C:21]=2[NH:20][CH2:19][CH2:18]3)=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 866030681H-Indole-7-carboxylic acid (4-tert-butyl-benzyl)-phenethyl-amide

Product 1

HCID 768468721h-Indole-7-carboxamide,n-[[4-(1,1-dimethylethyl)phenyl]methyl]-2,3-dihydro-n-(2-phenylethyl)-Yield 100%

Reagents, catalysts & solvents 1

HCID 176
Acetic Acid
Solvent

Conditions

Temperature
0 °C

Procedure

To a solution of 310 mg (0.76 mmol) of 1H-indole-7-carboxylic acid (4-tert-butyl-benzyl)-phenethyl-amide in 5 ml acetic acid cooled to 0° C. were added in portions 142 mg (2.26 mmol) of sodium cyano borohydride. The reaction mixture was stirred for 2 h at 0° C. and 2N aqueous sodium hydroxide solution was added until the reaction mixture was basic. The reaction mixture was extracted with diethyl ether. The combined organic layers were washed with saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered and the solvent was evaporated to yield 310 mg (100%) of product as a colorless oil. MS (ISP) 413.5 (M+H)+.

Workup

  1. extractionThe reaction mixture was extracted with diethyl ether
  2. washThe combined organic layers were washed with saturated aqueous sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-ddc5e73ea79b46359cfbe7aeb657b852
Source dataset
uspto-grants-2007_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07259183B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes