Hydrochloric Acid → HCID 22736374, compound

HRID 51502Notes

Reaction equation

HRID 51502 reaction equation
[C:1]([NH2:5])([CH3:4])([CH3:3])[CH3:2].Br[CH2:7][C:8]([C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:12][CH:11]=1)=[O:9].[ClH:23]>CC(O)C>[ClH:23].[O:16]([C:13]1[CH:12]=[CH:11][C:10]([C:8](=[O:9])[CH2:7][NH:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:15][CH:14]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6385Tert-ButylamineHCID 147976752-Bromo-1-(4-phenoxyphenyl)ethan-1-one

Product 1

HCID 22736374HCID 22736374, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
80 °C

Procedure

Tert-butylamine (15 ml) was added with stirring to a solution of 2-bromo-4′-phenoxyacetophenone (12.7 g, prepared by bromination of 4′-phenoxyacetophenone according to Tetrahedron Letters, 1993, 34, 3177) in propan-2-ol and the mixture heated at 80° C. for 3 hours. The mixture was cooled to 0C and concentrated hydrochloric acid (10 ml) added. The suspension was stirred at ambient temperature for 18 hours and the solid collected by filtration to give 4′-phenoxy-2-(tert-butylamino)acetophenone hydrochloride (3.75 g), m.p. 210-212° C.

Workup

  1. additionadded
  2. filtrationthe solid collected by filtration

Sources & evidence

ORD record
ord-10bcbe4c035a4e2398723ff776cfecad
Source dataset
uspto-grants-2004_03
Patent number
US06713474B2

Reaction notes

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