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

HRID 888592Notes

Reaction equation

HRID 888592 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-2a0c762d7dbf4ed292e806016539b26c
Source dataset
uspto-grants-2012_08
Patent number
US08247576B2

Reaction notes

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