Chloroform → HCID 21506608, compound

HRID 1287841Notes

Reaction equation

HRID 1287841 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:26]=[C:27]([O:31][CH3:32])[C:28]=1[O:29][CH3:30])[C:6]([NH:8][CH2:9][C:10]([NH:12][CH2:13][CH:14](O)[C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([O:23][CH3:24])[CH:16]=1)=O)=[O:7].C(Cl)(Cl)Cl.P(Cl)(Cl)(Cl)(Cl)Cl>O=[Pt]=O.CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:26]=[C:27]([O:31][CH3:32])[C:28]=1[O:29][CH3:30])[C:6]([NH:8][CH2:9][CH:10]1[C:20]2[C:15](=[CH:16][C:17]([O:23][CH3:24])=[C:18]([O:21][CH3:22])[CH:19]=2)[CH2:14][CH2:13][NH:12]1)=[O:7]

Participants

6

Reactant 3

HCID 6212ChloroformHCID 24819Phosphorus pentachlorideHCID 21506620HCID 21506620, compound

Product 1

HCID 21506608HCID 21506608, compound

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

4.48 g. of α-(3,4,5-trimethoxybenzamido)-N-[2-hydroxy-2-(3,4-dimethoxyphenyl)-ethyl]-acetamide [producible from 2-(3,4-dimethoxyphenyl)-2-hydroxyethylamine and 3,4,5-trimethoxybenzamidoacetyl chloride] is allowed to stand in 100 ml. of chloroform with 6.2 g. of phosphorus pentachloride for 3 days at 20°. The mixture is decomposed with ice water and washed several times with NaHCO3 solution. The chloroform solution is evaporated. The thus-obtained crude 1-(3,4,5-trimethoxybenzamidomethyl)-6,7-dimethoxy-isoquinoline is taken up in 50 ml. of methanol, combined with 400 mg. of PtO2, and hydrogenated at 20° and under normal pressure. The product is filtered and evaporated. Chromatography on silica gel (with chloroform/methanol 19:1) yields 1-(3,4,5-trimethoxybenzamidomethyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline; hydrochloride, m.p. 234°-236°.

Workup

  1. washwashed several times with NaHCO3 solution
  2. customThe chloroform solution is evaporated
  3. customThe thus-obtained crude 1-(3,4,5-trimethoxybenzamidomethyl)-6,7-dimethoxy-isoquinoline
  4. customhydrogenated at 20°
  5. filtrationThe product is filtered
  6. customevaporated

Sources & evidence

ORD record
ord-9825351244b54d71aaae1b13dc5d2394
Source dataset
uspto-grants-1976_10
Patent number
US03985881

Reaction notes

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