Methyl 5-(2-bromoacetyl)-2-(phenylmethoxy)benzoate → HCID 20347492, compound

HRID 1701262Notes

Reaction equation

HRID 1701262 reaction equation
[CH3:1][C:2]([NH2:14])([CH3:13])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]2[O:10][CH2:11][O:12][C:6]=2[CH:5]=1.[CH2:15]([O:22][C:23]1[CH:32]=[CH:31][C:30]([C:33](=[O:36])[CH2:34]Br)=[CH:29][C:24]=1[C:25]([O:27][CH3:28])=[O:26])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>O1CCCC1>[CH3:28][O:27][C:25]([C:24]1[CH:29]=[C:30]([C:33]([CH2:34][NH:14][C:2]([CH3:1])([CH3:13])[CH2:3][C:4]2[CH:9]=[CH:8][C:7]3[O:10][CH2:11][O:12][C:6]=3[CH:5]=2)=[O:36])[CH:31]=[CH:32][C:23]=1[O:22][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:26]

Participants

4

Reactant 2

HCID 11824614Methyl 5-(2-bromoacetyl)-2-(phenylmethoxy)benzoateHCID 130205981-(2H-1,3-Benzodioxol-5-yl)-2-methylpropan-2-amine

Product 1

HCID 20347492HCID 20347492, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 11.8 g (0.061 mole) of 1,1-dimethyl-2-(3,4-methylenedioxyphenyl)ethylamine in 151 ml of tetrahydrofuran was treated with 11.1 g (0.0306 mole) of methyl 2-benzyloxy-5-bromoacetylbenzoate. The resulting solution was stirred for 5.5 hours and allowed to stand for a further 48 hours after which it was cooled, the solid which had separated was filtered off and the filtrate was concentrated by evaporation. The filtered solid and the filtrate were then recombined and the mixture was covered with 100 ml of methanol, warmed to 35°, stirred at that temperature for 30 minutes and cooled. A solid which separated was filtered off, washed with methanol and air dried to give N-[1,1-dimethyl-2-(3,4-methylenedioxyphenyl)ethyl]aminomethyl 3-methoxycarbonyl-4-benzyloxyphenyl ketone as a white solid, m.p. 134°-141° C. (Yield 10.48 g, 72.0%).

Workup

  1. waitto stand for a further 48 hours
  2. temperatureafter which it was cooled
  3. customthe solid which had separated
  4. filtrationwas filtered off
  5. concentrationthe filtrate was concentrated by evaporation
  6. temperaturewarmed to 35°
  7. stirringstirred at that temperature for 30 minutes
  8. temperaturecooled
  9. customA solid which separated
  10. filtrationwas filtered off
  11. washwashed with methanol and air
  12. customdried

Sources & evidence

ORD record
ord-a7a1bed8045e4004a54de3fadc3ce966
Source dataset
uspto-grants-1980_03
Patent number
US04192805

Reaction notes

Loading…