Benzyl Alcohol → HCID 20434094, compound

HRID 1154620Notes

Reaction equation

HRID 1154620 reaction equation
[CH3:1][CH:2]([NH:14][CH2:15][CH:16]([OH:24])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[Cl:23])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[C:6]([O:12][CH3:13])[CH:5]=1.C(O)C1C=CC=CC=1.Cl>>[ClH:23].[CH3:1][CH:2]([NH:14][CH2:15][CH:16]([OH:24])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[Cl:23])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[C:6]([O:12][CH3:13])[CH:5]=1

Participants

4

Reactant 3

HCID 244Benzyl AlcoholHCID 313Hydrochloric Acid2×HCID 13365130HCID 13365130, compound

Product 1

HCID 20434094HCID 20434094, compound

Procedure

A mixture of the α-[(α-methyl-3,4-dimethoxyphenethyl]imino)-2-chloroacetophenone solution obtained in paragraph (2), 1.38 g of sodium borohydride and 30 ml of ethanol is treated in the same manner as described in Example 1-(3), whereby α-[(α-methyl-3,4-dimethoxyphenethylamino)methyl]-2-chlorobenzylalcohol [the mixture of two diastereoisomer] is obtained as a brown oil. Said benzylalcohol [i.e., the mixture of two diastereoisomers] is treated with ethanolic hydrogen chloride to convert it into its hydrochloride, and the hydrochloride is recrystallized from ethanol. The crystalline precipitates are collected by filtration (the filtrate is hereinafter referred to as "mother liquor"). 2.98 g of α-[(α-methyl-3,4-dimethoxyphenethylamino)methyl]-2-chlorobenzylalcohol hydrochloride [the diastereoisomer of M.p. 175°-176° C.] are thereby obtained.

Workup

  1. additionis treated in the same manner
  2. customis obtained as a brown oil
  3. additionthe mixture of two diastereoisomers]
  4. customthe hydrochloride is recrystallized from ethanol
  5. customThe crystalline precipitates
  6. filtrationare collected by filtration (the filtrate

Sources & evidence

ORD record
ord-6490ef32c5b7496f9f29bd5f076a31c0
Source dataset
uspto-grants-1984_12
Patent number
US04490392

Reaction notes

Loading…