Isopropanol → HCID 14518039, compound

HRID 2309638Notes

Reaction equation

HRID 2309638 reaction equation
C(OC(=O)[NH:5][CH2:6][CH2:7][N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][C:15]2[N:23]([CH2:24][C:25]3[S:26][CH:27]=[CH:28][CH:29]=3)[C:18]3=[N:19][CH:20]=[CH:21][CH:22]=[C:17]3[N:16]=2)[CH2:10][CH2:9]1)C.[OH-].[K+].[CH3:33][CH:34](O)[CH3:35]>>[C:34]1([CH2:24][N:23]2[C:18]3=[N:19][CH:20]=[CH:21][CH:22]=[C:17]3[N:16]=[C:15]2[CH2:14][CH:11]2[CH2:10][CH2:9][N:8]([CH2:7][C:6]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH2:13][CH2:12]2)[CH:35]=[CH:18][CH:17]=[CH:22][CH:33]=1.[S:26]1[CH:27]=[CH:28][CH:29]=[C:25]1[CH2:24][N:23]1[C:18]2=[N:19][CH:20]=[CH:21][CH:22]=[C:17]2[N:16]=[C:15]1[CH2:14][CH:11]1[CH2:12][CH2:13][N:8]([CH2:7][CH2:6][NH2:5])[CH2:9][CH2:10]1

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 14797Potassium HydroxideHCID 14518038HCID 14518038, compound

Product 2

HCID 14518039HCID 14518039, compoundYield 76%HCID 20037893HCID 20037893, compound

Procedure

A mixture of 20.7 parts of ethyl[2-[4-[[3-(2-thienylmethyl)-3H-imidazo[4,5-b]pyridin-2-yl]methyl]-1-piperidinyl]ethyl]carbamate, 22.1 parts of potassium hydroxide and 200 parts of 2-propanol was stirred and refluxed overnight. The reaction mixture was evaporated. Water was added to the residue. The product was extracted with dichloromethane. The extract was dried, filtered and evaporated, yielding 13 parts (76%) of 4-[[3-(2-thienylmethyl)-3H-imidazo[4,5-b]pyridin-2-yl]methyl]-1-piperidinethanamine (325).

Workup

  1. temperaturerefluxed overnight
  2. customThe reaction mixture was evaporated
  3. additionWater was added to the residue
  4. extractionThe product was extracted with dichloromethane
  5. customThe extract was dried
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-c43130dafa8845d8bc117fee4534afdf
Source dataset
uspto-grants-1987_09
Patent number
US04695575

Reaction notes

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