Dopamine Hydrochloride → HCID 70505289, compound

HRID 27154Notes

Reaction equation

HRID 27154 reaction equation
Cl.[OH:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[OH:12])[CH2:6][CH2:7][NH2:8].C([O:15][CH:16]([O:29]CC)[CH2:17][NH:18][C:19]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20])C>C(O)CCC.O>[C:16]([OH:29])(=[O:15])[CH3:17].[CH2:22]([O:21][C:19]([NH:18][CH2:17][CH:16]1[C:9]2[C:5](=[CH:4][C:3]([OH:2])=[C:11]([OH:12])[CH:10]=2)[CH2:6][CH2:7][NH:8]1)=[O:20])[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

5

Reactant 2

HCID 65340Dopamine HydrochlorideHCID 292521Benzyl 2,2-diethoxyethylcarbamate

Product 1

HCID 70505289HCID 70505289, compoundYield 41.3%

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 962WaterSolvent

Procedure

A solution of 3,4-dihydroxyphenethylamine hydrochloride (2.17 g) and N-benzyloxycarbonylaminoacetaldehyde diethyl acetal (4.0 g) in a mixture of n-butyl alcohol (20 ml) and water (3.5 ml) was refluxed for 4.5 hours. After the reaction, the solvent was distilled off under reduced pressure. To the residue were added water (15 ml) and sodium acetate. A precipitating oil was separated from the aqueous layer and chloroform was added thereto. The mixture was allowed to stand to give crystals. The crystals were collected by filtration, washed with chloroform and recrystallized twice from a mixture of methanol and ether to give 1(N-benzyloxycarbonylaminomethyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline acetate (1.2 g), mp 158° to 162° C. (dec).

Workup

  1. temperaturewas refluxed for 4.5 hours
  2. customAfter the reaction
  3. distillationthe solvent was distilled off under reduced pressure
  4. additionTo the residue were added water (15 ml) and sodium acetate
  5. customA precipitating oil was separated from the aqueous layer and chloroform
  6. additionwas added
  7. customto give crystals
  8. filtrationThe crystals were collected by filtration
  9. washwashed with chloroform
  10. customrecrystallized twice from a mixture of methanol and ether

Sources & evidence

ORD record
ord-0e61cd7902804406b1b63982cba458bc
Source dataset
uspto-grants-1980_09
Patent number
US04220647

Reaction notes

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