Hydrochloric Acid → HCID 86735771, compound

HRID 839611Notes

Reaction equation

HRID 839611 reaction equation
[ClH:1].[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[CH:16](OCC)[CH2:17][N:18](C(OCC1C=CC=CC=1)=O)[C:19]1[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=1)C.Cl>O>[OH2:2].[ClH:1].[ClH:1].[N:22]1[CH:21]=[CH:20][C:19]([NH:18][CH2:17][CH:16]2[C:9]3[C:5](=[CH:4][C:3]([OH:2])=[C:11]([OH:12])[CH:10]=3)[CH2:6][CH2:7][NH:8]2)=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 65340Dopamine HydrochlorideHCID 20323724HCID 20323724, compound

Product 1

HCID 86735771HCID 86735771, compoundYield 158%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 3,4-dihydroxyphenethylamine hydrochloride (0.53 g.), N-benzyloxycarbonyl-N-(4-pyridyl)aminoacetaldehyde diethyl acetal (1.2 g.) and conc. hydrochloric acid (1 ml.) in water (6 ml.) was refluxed for 8 hours at 100° C. The reaction mixture was concentrated under reduced pressure and the crystalline residue was recrystallized from a mixture of methanol and ether to give 1-(4-pyridyl)aminomethyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline dihydrochloride monohydrate (0.8 g.), mp 172° to 176° C (dec.).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe crystalline residue was recrystallized from a mixture of methanol and ether

Sources & evidence

ORD record
ord-df1cb876df094dedaa2ce30f9bf1ce42
Source dataset
uspto-grants-1978_06
Patent number
US04096263

Reaction notes

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