Benzyl Alcohol → HCID 73164954, compound

HRID 371482Notes

Reaction equation

HRID 371482 reaction equation
[ClH:1].[CH3:2][O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:13]=1[O:14][CH3:15])[CH2:10][NH:9][CH:8]([C:16]([OH:18])=[O:17])[CH2:7]2.[CH2:19](O)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.Cl>CO>[ClH:1].[CH3:2][O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:13]=1[O:14][CH3:15])[CH2:10][NH:9][CH:8]([C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17])[CH2:7]2

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 313Hydrochloric AcidHCID 122480666,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid hydrochloride

Product 1

HCID 73164954HCID 73164954, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1,2,3,4-tetrahydro-6,7-dimethoxy-3-isoquinolinecarboxylic acid, hydrochloride (S-form) and 600 ml of benzyl alcohol was saturated with hydrogen chloride gas. The temperature rose to 45° C. The mixture was stirred at room temperature for three days. A relatively small amount of solid was filtered off and the filtrate was treated with ca 2-liters of ether to precipitate crude product; wt 37.5 g; yield, 83%. Purification was effected by treatment with excess saturated sodium bicarbonate, extraction of base into ethyl acetate and precipitation of hydrochloride salt with HCl gas. Recrystallization from methanol-ether gave pure product; mp 255°-260° C.; [α]D 23=-81.3° (1.0% MeOH); tlc (20% MeOH-CHCl3 /SiO2) one spot Rf 0.8.

Workup

  1. customrose to 45° C
  2. filtrationA relatively small amount of solid was filtered off
  3. additionthe filtrate was treated with ca 2-liters of ether
  4. customto precipitate crude product
  5. customyield
  6. customPurification
  7. extractionwas effected by treatment with excess saturated sodium bicarbonate, extraction of base into ethyl acetate and precipitation of hydrochloride salt with HCl gas
  8. customRecrystallization from methanol-ether
  9. customgave pure product

Sources & evidence

ORD record
ord-96e4a3298f784b8d8a1474c63ecf727f
Source dataset
uspto-grants-1985_07
Patent number
US04532342

Reaction notes

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