Hydrochloric Acid → 3-Chloro-alpha-[[[1,1-dimethylethyl]amino]methyl]benzenemethanol hydrochloride salt

HRID 2072771Notes

Reaction equation

HRID 2072771 reaction equation
B.CSC.[CH3:5][C:6]([NH:9][C:10](=O)[CH:11]([OH:19])[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[CH:13]=1)([CH3:8])[CH3:7].CO.Cl>O1CCCC1>[ClH:18].[Cl:18][C:14]1[CH:13]=[C:12]([CH:11]([CH2:10][NH:9][C:6]([CH3:8])([CH3:7])[CH3:5])[OH:19])[CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 12423031(Dimethyl sulfide)trihydroboronHCID 19913633N-[1,1-dimethylethyl]-3-chloro-alpha-hydroxybenzeneacetamide

Product 1

HCID 199136423-Chloro-alpha-[[[1,1-dimethylethyl]amino]methyl]benzenemethanol hydrochloride salt

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Borane-methyl sulphide (2.15 g, 2.7 ml, 4 equivs.) was added dropwise, under nitrogen, to a stirred solution of N-[1,1-dimethylethyl]-3-chloro-α-hydroxybenzene acetamide (1.71 g) in dry tetrahydrofuran. The resulting solution was stirred and heated under reflux for 2 h., cooled, and treated with methanol (1 ml). The reaction mixture was heated under reflux for 1 h., cooled, treated with methanolic hydrogen chloride, and the solvent evaporated to give 3-chloro-α-[[[1,1-dimethylethyl]amino]methyl]benzenemethanol hydrochloride salt, 1.5 g, m.p. 165°-175° C.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 2 h.
  3. temperaturecooled
  4. temperatureThe reaction mixture was heated
  5. temperatureunder reflux for 1 h.
  6. temperaturecooled
  7. customthe solvent evaporated

Sources & evidence

ORD record
ord-b4b848ada2a0433f9da617f38c6baf59
Source dataset
uspto-grants-1990_04
Patent number
US04914202

Reaction notes

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