Hydrochloric Acid → 1-[(3,4-Diethoxyphenyl)methyl]-6,7-bis[(propan-2-yl)oxy]-1,2,3,4-tetrahydroisoquinoline--hydrogen chloride (1/1)

HRID 325618Notes

Reaction equation

HRID 325618 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:26]=[CH:27][C:28]=1[O:29][CH2:30][CH3:31])[CH2:7][CH:8]1[C:17]2[C:12](=[CH:13][C:14]([O:22][CH:23]([CH3:25])[CH3:24])=[C:15]([O:18][CH:19]([CH3:21])[CH3:20])[CH:16]=2)[CH2:11][CH2:10][NH:9]1)[CH3:2].[ClH:32]>C(O)C.C(OCC)C>[ClH:32].[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:26]=[CH:27][C:28]=1[O:29][CH2:30][CH3:31])[CH2:7][CH:8]1[C:17]2[C:12](=[CH:13][C:14]([O:22][CH:23]([CH3:24])[CH3:25])=[C:15]([O:18][CH:19]([CH3:21])[CH3:20])[CH:16]=2)[CH2:11][CH2:10][NH:9]1)[CH3:2]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 3052873HCID 3052873, compound

Product 1

HCID 30528721-[(3,4-Diethoxyphenyl)methyl]-6,7-bis[(propan-2-yl)oxy]-1,2,3,4-tetrahydroisoquinoline--hydrogen chloride (1/1)Yield 99%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

81.5 g (0.019 mole) of 1-(3',4'-diethoxybenzyl)-6,7-diisopropoxy-1,2,3,4-tetrahydroisoquinoline was dissolved in 50 ml ethanol. 10 ml of a solution of hydrochloric acid in diethyl ether was added with agitation and cooling in an ice/water bath, (to pH=2). The solvent was removed under reduced pressure, the residue was stirred in suspension in 100 ml of isopropyl ether for a few minutes, excess solvent removed and the product dried to give 8.75 g of the title hydrochloride. Yield=99%. m.p. 158° C.

Workup

  1. temperaturecooling in an ice/water bath
  2. customThe solvent was removed under reduced pressure
  3. customexcess solvent removed
  4. customthe product dried

Sources & evidence

ORD record
ord-cca71868a396458ab4fb75c1968dd8ad
Source dataset
uspto-grants-1984_04
Patent number
US04442108

Reaction notes

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