Triethylamine → HCID 54161733, compound

HRID 2211429Notes

Reaction equation

HRID 2211429 reaction equation
C(N(CC)CC)C.[CH3:8][O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH2:16][C:17](Cl)=[O:18].Cl.[C:21]1([C:27]2([C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)[CH2:35][CH:34]=[C:33]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=3[O:42][CH3:43])[C@H:32]3[C@@H:28]2[CH2:29][NH:30][CH2:31]3)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(Cl)Cl>[C:44]1([C:27]2([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH2:35][CH:34]=[C:33]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=3[O:42][CH3:43])[C@H:32]3[C@@H:28]2[CH2:29][N:30]([C:17](=[O:18])[CH2:16][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[O:9][CH3:8])[CH2:31]3)[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1795022-(2-Methoxyphenyl)acetyl chlorideHCID 22857049HCID 22857049, compound

Product 1

HCID 54161733HCID 54161733, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

1.5 cm3 of triethylamine and then 1.6 g of (2-methoxyphenyl)-acetyl chloride are added to a solution of 1.5 g of (3aS,7aR)-4,4-diphenyl-7-(2-methoxyphenyl)-2,3,3a,4,5,7a-hexahydro-isoindole hydrochloride in 20 cm3 of methylene chloride, cooled to 0° C. The mixture is stirred at room temperature for 15 hours; the reaction mixture is washed with twice 40 cm3 of water, dried over magnesium sulphate and concentrated to dryness under reduced pressure (2.7 kPa). The residue is chromatographed over a Merck silica gel column (particle size 0.04-0.06 mm, diameter 3.6 cm, height 25 cm) by eluting under a pressure of 0.5 bar of nitrogen with a mixture of cyclohexane and ethyl acetate (75/25 by volume) and collecting fractions of 25 cm3. Fractions 14 to 28 are combined and concentrated to dryness under reduced pressure (2.7 kPa). The yellow foam obtained is recrystallised from 10 cm3 of cyclohexane to give 0.38 g of (3aS,7aR)-4,4-diphenyl-2-[(2-methoxyphenyl)-acetyl]-7-(2-methoxyphenyl)-2,3,3a,4,5,7a-hexahydro-isoindole in the form of a beige solid which melts at 142° C.

Workup

  1. washthe reaction mixture is washed with twice 40 cm3 of water
  2. dry with materialdried over magnesium sulphate
  3. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  4. customThe residue is chromatographed over a Merck silica gel column (particle size 0.04-0.06 mm, diameter 3.6 cm, height 25 cm)
  5. washby eluting under a pressure of 0.5 bar of nitrogen with a mixture of cyclohexane and ethyl acetate (75/25 by volume)
  6. customcollecting fractions of 25 cm3
  7. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  8. customThe yellow foam obtained
  9. customis recrystallised from 10 cm3 of cyclohexane

Sources & evidence

ORD record
ord-c245269eed36442a91510dab057d7228
Source dataset
uspto-grants-1995_10
Patent number
US05463077

Reaction notes

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