Benzyl Alcohol → HCID 20434095, compound

HRID 1154624Notes

Reaction equation

HRID 1154624 reaction equation
[CH3:1][CH:2]([NH:13][CH2:14][CH:15]([OH:23])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[Cl:22])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]2[O:10][CH2:11][O:12][C:6]=2[CH:5]=1.C(O)C1C=CC=CC=1.Cl>>[ClH:22].[CH3:1][CH:2]([NH:13][CH2:14][CH:15]([OH:23])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[Cl:22])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]2[O:10][CH2:11][O:12][C:6]=2[CH:5]=1

Participants

4

Reactant 3

HCID 244Benzyl AlcoholHCID 313Hydrochloric Acid2×HCID 13365133HCID 13365133, compound

Product 1

HCID 20434095HCID 20434095, compound

Procedure

A mixture of the α-(α-methyl-3,4-methylenedioxyphenethylimino)-B 2-chloroacetophenone solution obtained in paragraph (2), 1.73 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-methylenedioxyphenethylamino)methyl]-2-chlorobenzylalcohol [the mixture of two diastereoisomers] is obtained as a crude 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 methanol. The crystalline precipitates are collected by filtration (the filtrate is hereinafter referred to as "mother liquor"). 5.0 g of α-[(α-methyl-3,4-methylenedioxyphenethylamino)methyl]-2-chlorobenzylalcohol hydrochloride [the diastereoisomer of M.p. 202°-203° C. (decomp.)] are thereby obtained.

Workup

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

Sources & evidence

ORD record
ord-965263aec1e04aa9b05bcff29131ee18
Source dataset
uspto-grants-1984_12
Patent number
US04490392

Reaction notes

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