1-Butanol → 1-(N-benzyloxycarbonyl-N-isopropylaminomethyl)-7,8-dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrochloride

HRID 27150

Reaction equation

HRID 27150 reaction equation
C(O[CH:4](OCC)[CH2:5][N:6]([C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11])[CH:7]([CH3:9])[CH3:8])C.[ClH:23].[OH:24][C:25]1[CH:26]=[C:27]([CH:31]=[CH:32][C:33]=1[OH:34])[CH2:28][CH2:29][NH2:30].C(O)CCC>O>[ClH:23].[CH2:13]([O:12][C:10]([N:6]([CH2:5][CH:4]1[C:26]2[C:27](=[CH:31][CH:32]=[C:33]([OH:34])[C:25]=2[OH:24])[CH2:28][CH2:29][NH:30]1)[CH:7]([CH3:8])[CH3:9])=[O:11])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 2631-ButanolHCID 65340Dopamine HydrochlorideHCID 20460589N-benzyloxycarbonyl-N-isopropylaminoacetaldehyde diethyl acetal

Product 1

HCID 204605571-(N-benzyloxycarbonyl-N-isopropylaminomethyl)-7,8-dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrochlorideYield 16.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

N-benzyloxycarbonyl-N-isopropylaminoacetaldehyde diethyl acetal (9 g) and 3,4-dihydroxyphenethylamine hydrochloride (4.5 g) were added to a mixture of n-butyl alcohol (100 ml) and water (15 ml) and then the mixture was refluxed for 6 hours. The above-mentioned acetal (2 g) was added thereto and the resultant mixture was refluxed for 1.5 hours. The solvent was distilled off from the reaction mixture. To the residue was added a mixed solvent of isopropyl alcohol, methanol and ether. The crystals obtained were recrystallized from the same mixed solvent to give 1-(N-benzyloxycarbonyl-N-isopropylaminomethyl)-7,8-dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (1.6 g), mp 200° to 205° C. (dec). The mother liquor was concentrated and allowed to stand to give 1-(N-benzyloxycarbonyl-N-isopropylaminomethyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (4.4 g), colorless crystals, mp 207° to 210° C. (dec).

Workup

  1. temperaturethe mixture was refluxed for 6 hours
  2. distillationThe solvent was distilled off from the reaction mixture
  3. additionTo the residue was added a mixed solvent of isopropyl alcohol, methanol and ether
  4. customThe crystals obtained
  5. customwere recrystallized from the same mixed solvent

Sources & evidence

ORD record
ord-b563cb76af2848e398bcfb1d5edeaa9c
Source dataset
uspto-grants-1980_09
Patent number
US04220647

Linked notes

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