Benzyl Alcohol → HCID 20434083, compound

HRID 1154623Notes

Reaction equation

HRID 1154623 reaction equation
[CH3:1][CH:2]([NH:13][CH2:14][CH:15]([OH:24])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[O:22][CH3:23])[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.[ClH:33]>>[ClH:33].[CH3:1][CH:2]([NH:13][CH2:14][CH:15]([OH:24])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[O:22][CH3:23])[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 13365131HCID 13365131, compound

Product 1

HCID 20434083HCID 20434083, compound

Procedure

A mixture of the α-(α-methyl-3,4-methylenedioxyphenethylimino)-2-methoxyacetophenone 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-methoxybenzylalcohol [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 an aqueous acetone. The crystalline precipitates are collected by filtration (the filtrate is hereinafter referred to as "mother liquor"). 5.4 g of α-[(α-methyl-3,4-methylenedioxyphenethylamino)methyl]-2-methoxybenzylalcohol hydrochloride [the diastereoisomer of M.p. 152°-153° C.] 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 an aqueous acetone
  5. customThe crystalline precipitates
  6. filtrationare collected by filtration (the filtrate

Sources & evidence

ORD record
ord-e48071a4679a4614ab540159ed9b4ee9
Source dataset
uspto-grants-1984_12
Patent number
US04490392

Reaction notes

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