Methylamine → 1-(4-Bromophenyl)-2-methylaminoethanol

HRID 924725Notes

Reaction equation

HRID 924725 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:10][O:9]2)=[CH:4][CH:3]=1.[CH3:11][NH2:12]>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:9])[CH2:10][NH:12][CH3:11])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 6329MethylamineHCID 1194602-(4-Bromophenyl)oxirane

Product 1

HCID 219434331-(4-Bromophenyl)-2-methylaminoethanol

Procedure

A solution of 2-(4-bromophenyl)-oxirane (0.5 g, 2.51 mmol) in methylamine (6.6 ml, 33% by volume in ethanol, 25.12 mmol) was stirred at room temperature under an atmosphere of nitrogen. After 18 hours the solvent was removed in vacuo and the residue was purified over flash silica eluting with dichloromethane: methanol:acetic acid:water (120:15:3:2) to afford the desired compound as the acetic acid salt. Further purification over a Phenomenex_Strata_SCX column eluting with methanol followed by 2N ammonia in methanol gave the desired product. LC/MS: (PS-B3) Rt 2.52 [M+H]+ 230.

Workup

  1. customAfter 18 hours the solvent was removed in vacuo
  2. customthe residue was purified over flash silica eluting with dichloromethane: methanol:acetic acid:water (120:15:3:2)

Sources & evidence

ORD record
ord-8373886837454c999b407ed5e97eee32
Source dataset
uspto-grants-2016_03
Patent number
US09283226B2

Reaction notes

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