Sodium Hydroxide → HCID 20239755, compound

HRID 1388396Notes

Reaction equation

HRID 1388396 reaction equation
[C:1]1([C:7]([NH:20][CH2:21][C:22]2[N:23]([CH2:27][CH:28]3[CH2:33][CH2:32][N:31](C=O)[CH2:30][CH2:29]3)[CH:24]=[CH:25][N:26]=2)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>CO>[C:1]1([C:7]([NH:20][CH2:21][C:22]2[N:23]([CH2:27][CH:28]3[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]3)[CH:24]=[CH:25][N:26]=2)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 20239786HCID 20239786, compound

Product 1

HCID 20239755HCID 20239755, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 4-[(2-triphenylmethylaminomethyl-1H-imidazol-1-yl)methyl]-1-piperidinecarboxaldehyde (0.48 g, 0.00103 M), 2 N sodium hydroxide (24 ml) and methanol (24 ml) was heated at 50° C. for 4 hrs. The reaction was concentrated to about 20 ml at room temperature and extracted with ethylacetate. The extracts, dried over sodium sulfate, was stripped to dryness and purified on preparative thin layer chromatography plates to give 4-[(2-triphenylmethylaminomethyl-1H-imidazol-1-yl)methyl]-piperidine (0.167 g, 37% yield).

Workup

  1. concentrationThe reaction was concentrated to about 20 ml at room temperature
  2. extractionextracted with ethylacetate
  3. dry with materialThe extracts, dried over sodium sulfate
  4. custompurified on preparative thin layer chromatography plates

Sources & evidence

ORD record
ord-9f991641dc6e4ba1baf471f7379f40c4
Source dataset
uspto-grants-1984_02
Patent number
US04431653

Reaction notes

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