Hydrochloric Acid → HCID 12915859, compound

HRID 543490Notes

Reaction equation

HRID 543490 reaction equation
[OH:1][CH:2]([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)[CH:3]([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)[CH3:4].[ClH:43].[H][H]>[C].[Pd].CO>[ClH:43].[OH:1][CH:2]([C:21]1[CH:26]=[CH:25][C:24]([OH:27])=[C:23]([OH:35])[CH:22]=1)[CH:3]([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)[CH3:4]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 12915872HCID 12915872, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 12915859HCID 12915859, compoundYield 61.4%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent2×

Procedure

To 130 ml of a methanol solution containing 1.75 g of 1-[3-hydroxy-3-(3,4-dibenzyloxyphenyl)-2-propyl]-4-(2-keto-1-benzimidazolinyl)-piperidine is added 1 ml of a methanol solution containing 120 mg of hydrogen chloride, and, 0.2 g of palladium carbon is added thereto. The mixture is vigorously shaked in a hydrogen stream at room temperature. After stirring overnight, the catalyst is removed by filtration and the mother liquor is concentrated under reduced pressure. The resultant oily material is crystallized by adding a small amount of n-butanol. The crystals are collected by filtration, and dried to obtain 1.06 g of the crude crystals. Recrystallization thereof from n-butanol yields 0.8 g of 1-[3-hydroxy-3-(3,4-dihydroxyphenyl)-2-propyl]-4-(2-keto-1-benzimidazolinyl)-piperidine hydrochloride having m.p. 187°-189° C.

Workup

  1. additionis added
  2. customthe catalyst is removed by filtration
  3. concentrationthe mother liquor is concentrated under reduced pressure
  4. customThe resultant oily material is crystallized
  5. additionby adding a small amount of n-butanol
  6. filtrationThe crystals are collected by filtration
  7. customdried
  8. customto obtain 1.06 g of the crude crystals
  9. customRecrystallization

Sources & evidence

ORD record
ord-87a73943e03f4d86a681f6e0f33a4d66
Source dataset
uspto-grants-1984_05
Patent number
US04446141

Reaction notes

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