Phenylacetyl chloride → HCID 67915864, compound

HRID 1029942Notes

Reaction equation

HRID 1029942 reaction equation
C(N(CC)CC)C.[C:8]1([CH2:14][C:15](Cl)=[O:16])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.Cl.[Cl:19][C:20]1[CH:21]=[C:22]([C:26]2([C:36]3[CH:41]=[CH:40][CH:39]=[C:38]([Cl:42])[CH:37]=3)[CH:34]3[CH:30]([CH2:31][NH:32][CH2:33]3)[C:29](=[O:35])[CH2:28][CH2:27]2)[CH:23]=[CH:24][CH:25]=1>ClCCl>[Cl:42][C:38]1[CH:37]=[C:36]([C:26]2([C:22]3[CH:23]=[CH:24][CH:25]=[C:20]([Cl:19])[CH:21]=3)[CH:34]3[CH:30]([CH2:31][N:32]([C:15](=[O:16])[CH2:14][C:8]4[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=4)[CH2:33]3)[C:29](=[O:35])[CH2:28][CH2:27]2)[CH:41]=[CH:40][CH:39]=1

Participants

5

Reactant 3

HCID 7679Phenylacetyl chlorideHCID 8471TriethylamineHCID 67916022HCID 67916022, compound

Product 1

HCID 67915864HCID 67915864, compoundYield 16.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

Triethylamine (0.45 cc) and then phenylacetyl chloride (0.49 g) are added to a solution of 7,7-bis-(3-chlorophenyl)-4-perhydroisoindolone hydrochloride (1.06 g) in dichloromethane (20 cc) cooled to +4° C. The reactio mixture is stirred for 2 hours at 25° C. and then washed with water (3×30 cc) and with saturated sodium chloride solution (3×30 cc). The organic phase is dried over magnesium sulphate and filtered and the filtrate is concentrated to dryness under reduced pressure (2.7 kPa). The residue is chromatographed on a silica gel column (particle size 0.04-0.063 mm, diameter 2.2 cm, height 23 cm), eluting under a nitrogen pressure of 0.5 bar with a mixture of cyclohexane and ethyl acetate (55/45 by volume) and collecting 15 cc fractions. Fractions 7 to 18 are concentrated to dryness under reduced pressure (2.7 kPa) and the residue is crystallized from acetonitrile. The crystals are drained, washed with isopropyl ether and dried. (3aRS,7aRS)-7,7-bis-(3-chlorophenyl)-2-(phenylacetyl)-4-perhydroisoindolone (0.21 g) is obtained. m.p.=160° C.

Workup

  1. temperaturecooled to +4° C
  2. washwashed with water (3×30 cc) and with saturated sodium chloride solution (3×30 cc)
  3. dry with materialThe organic phase is dried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationthe filtrate is concentrated to dryness under reduced pressure (2.7 kPa)
  6. customThe residue is chromatographed on a silica gel column (particle size 0.04-0.063 mm, diameter 2.2 cm, height 23 cm)
  7. washeluting under a nitrogen pressure of 0.5 bar
  8. additionwith a mixture of cyclohexane and ethyl acetate (55/45 by volume)
  9. customcollecting 15 cc fractions
  10. concentrationFractions 7 to 18 are concentrated to dryness under reduced pressure (2.7 kPa)
  11. customthe residue is crystallized from acetonitrile
  12. washwashed with isopropyl ether
  13. customdried

Sources & evidence

ORD record
ord-d839d8bdd916410fb6fc616c239e6c16
Source dataset
uspto-grants-1992_04
Patent number
US05102667

Reaction notes

Loading…