4-(4-Methoxyphenyl)butan-2-amine → HCID 12850096, compound

HRID 1614741Notes

Reaction equation

HRID 1614741 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([CH:6]2[O:8][CH2:7]2)=[CH:4][C:3]=1[S:11][CH3:12].[CH3:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][CH:23]([NH2:25])[CH3:24])=[CH:17][CH:16]=1>C1C=CC=CC=1>[CH3:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][CH:23]([NH:25][CH2:7][CH:6]([C:5]2[CH:9]=[CH:10][C:2]([CH3:1])=[C:3]([S:11][CH3:12])[CH:4]=2)[OH:8])[CH3:24])=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 4102024-(4-Methoxyphenyl)butan-2-amineHCID 12850095HCID 12850095, compound

Product 1

HCID 12850096HCID 12850096, compoundYield 29.2%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
115 °C

Procedure

A mixture of 6 g of 4-methyl-3-methylthiostyrene oxide and 7 g of 3-(4-methoxyphenyl)-1-methylpropylamine was heated to 115° C. for 3 hours. After the reaction was over, the reaction mixture was dissolved in 100 ml of benzene and after washing twice each time with 200 ml of water, the benzene layer was purified by a silica gel column chromatography (eluate: a mixture of benzene, ethyl acetate, and methanol (4:3:1 by volume ratio) to provide 3.5 g of amorphous α-{[3-(4-methoxyphenyl)-1-methylpropylamino]methyl}-4-methyl-3-methylthiobenzenemethanol.

Workup

  1. washafter washing twice each time with 200 ml of water
  2. customthe benzene layer was purified by a silica gel column chromatography (eluate
  3. additiona mixture of benzene, ethyl acetate, and methanol (4:3:1 by volume ratio)

Sources & evidence

ORD record
ord-eebc6ba1663b45e2aa58c09b544997f8
Source dataset
uspto-grants-1993_03
Patent number
US05198587

Reaction notes

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