HCID 12915870, compound → HCID 12875762, compound

HRID 543488Notes

Reaction equation

HRID 543488 reaction equation
[ClH:1].[OH:2][CH:3]([C:21]1[CH:26]=[CH:25][C:24]([O:27]CC2C=CC=CC=2)=[C:23]([O:35]CC2C=CC=CC=2)[CH:22]=1)[CH2:4][N:5]1[CH2:10][CH2:9][CH:8]([N:11]2[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=3[NH:13][C:12]2=[O:20])[CH2:7][CH2:6]1.[H][H]>CO.[C].[Pd]>[ClH:1].[OH:2][CH:3]([C:21]1[CH:26]=[CH:25][C:24]([OH:27])=[C:23]([OH:35])[CH:22]=1)[CH2:4][N:5]1[CH2:6][CH2:7][CH:8]([N:11]2[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=3[NH:13][C:12]2=[O:20])[CH2:9][CH2:10]1

Participants

5

Reactant 2

HCID 12915870HCID 12915870, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 12875762HCID 12875762, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

2.31 g of 1-[2-hydroxy-2-(3,4-dibenzyloxyphenyl)-1-ethyl]-4-(2-keto-1-benzimidazolinyl)-piperidine hydrochloride is dissolved in 250 ml of methanol. 0.3 g of palladium carbon (10%) is added thereto, and the mixture is vigorously shaked in a hydrogen stream under atmospheric pressure. After discontinuation of the absorption of hydrogen, the catalyst is filtered off, and the mother liquor is concentrated. To the residual syrup is added ethyl acetate, and the mixture is well stirred. The mixture is filtered to obtain powdered product, and the product is washed with ethyl acetate and dried to obtain 1.52 g of 1-[2-hydroxy-2- (3,4-dihydroxyphenyl)-1-ethyl]-4-(2-keto-1-benzimidazolinyl)-piperidine hydrochloride as amorphous powder. When subjected to thin layer chromatography using a lower layer of a mixture of chloroform/methanol/acetic acid/water (10/10/1/10), this product provides single spot at Rf =0.15.

Workup

  1. customAfter discontinuation of the absorption of hydrogen
  2. filtrationthe catalyst is filtered off
  3. concentrationthe mother liquor is concentrated
  4. additionTo the residual syrup is added ethyl acetate
  5. filtrationThe mixture is filtered
  6. customto obtain powdered product
  7. washthe product is washed with ethyl acetate
  8. customdried

Sources & evidence

ORD record
ord-756b32047b07466583cbcd3b6ea236f4
Source dataset
uspto-grants-1984_05
Patent number
US04446141

Reaction notes

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