Carbon Dioxide → HCID 21476698, compound

HRID 2293340Notes

Reaction equation

HRID 2293340 reaction equation
[Mg].C(Br)C.II.[CH:7]([N:10]([CH2:14][CH2:15][CH:16]([C:23]1[CH:28]=[C:27](Br)[CH:26]=[CH:25][C:24]=1[O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH:11]([CH3:13])[CH3:12])([CH3:9])[CH3:8].[C:38](=[O:40])=[O:39].[Cl-:41].[NH4+]>C(OCC)C.O1CCCC1>[ClH:41].[CH:7]([N:10]([CH2:14][CH2:15][CH:16]([C:23]1[CH:28]=[C:27]([C:38]([OH:40])=[O:39])[CH:26]=[CH:25][C:24]=1[O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH:11]([CH3:13])[CH3:12])([CH3:9])[CH3:8]

Participants

9

Reactant 6

HCID 280Carbon DioxideHCID 807IodineHCID 6332Ethyl Bromide2×HCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 129724153-(2-(Benzyloxy)-5-bromophenyl)-N,N-diisopropyl-3-phenylpropan-1-amine

Product 1

HCID 21476698HCID 21476698, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of magnesium (12.2 g, 0.5 mole), ethyl bromide (2 g), and iodine (a small crystal) in dry diethyl ether (200 mL) was warmed until the reaction started. (+)-N,N-diisopropyl-3-(2-benzyloxy-5-bromophenyl)-3-phenylpropylamine (45.6 g, 0.095 mole) and ethyl bromide (32.7 g, 0.3 mole) dissolved in dry diethyl ether (250 mL) were then added dropwise under nitrogen atmosphere. The mixture was refluxed for 1.5 h and then cooled in an acetone/dry-ice bath, whereupon powdered dry ice (≈100 g) was added gently. Tetrahydrofuran was added when needed to prevent the mixture from solidification. The reaction mixture was stirred for 0.5 h when ammonium chloride (200 mL, 20% w/w) was added. The mixture was stirred vigorously until two transparent phases were formed, and then filtered through a pad of Celatom. The aqueous layer was washed with diethyl ether and then acidified with hydrochloric acid to pH 1. The precipitated semi-crystalline gum was washed with water, and then transferred to a round bottom flask. The product was dried by co-evaporation with acetone, benzene, toluene, diisopropyl ether and methanol, successively. The title compound (35.1 g, 77%) was isolated as friable shiny flakes and used without any further purification.

Workup

  1. temperaturewas warmed until the reaction
  2. additionwere then added dropwise under nitrogen atmosphere
  3. temperatureThe mixture was refluxed for 1.5 h
  4. additionwas added gently
  5. additionwas added
  6. customwere formed
  7. filtrationfiltered through a pad of Celatom
  8. washThe aqueous layer was washed with diethyl ether
  9. washThe precipitated semi-crystalline gum was washed with water
  10. customtransferred to a round bottom flask
  11. dry with materialThe product was dried by co-evaporation with acetone, benzene, toluene, diisopropyl ether and methanol

Sources & evidence

ORD record
ord-b3bf5ea3c6b64fd0a474a08d416e1ebb
Source dataset
uspto-grants-1997_11
Patent number
US05686464

Reaction notes

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