Triethylamine → HCID 67745322, compound

HRID 375489

Reaction equation

HRID 375489 reaction equation
[CH3:1][N:2]([CH3:13])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][C:10]([OH:12])=O.Cl.[C:15]1([C:21]2([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH:29]3[CH:25]([CH2:26][NH:27][CH2:28]3)[S:24][CH2:23][CH2:22]2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(N(CC)CC)C>ClCCl>[CH3:13][N:2]([CH3:1])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][C:10]([N:27]1[CH2:28][CH:29]2[C:21]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH2:22][CH2:23][S:24][CH:25]2[CH2:26]1)=[O:12]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 204661092-(2-(Dimethylamino)phenyl)acetic acidHCID 67745331(4aRS,7aRS)4,4-diphenylperhydrothiopyrano[2,3-c]pyrrole hydrochloride

Product 1

HCID 67745322HCID 67745322, compoundYield 78.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1.18 g of N,N'-carbonyldiimidazole are added to a solution of 1.16 g of 2-dimethylaminophenylacetic acid in 20 cm3 of dry dichloromethane. The mixture is stirred for 30 minutes at +5° C. and then a solution of 2.0 g of (4aRS,7aRS)-4,4-diphenylperhydrothiopyrano[2,3-c]pyrrole hydrochloride and 1.83 cm3 of triethylamine in 20 cm3 of dichloromethane is added. The reaction mixture is stirred for 1 hour at 20° C. and is then washed twice with 50 cm3 of water and dried over magnesium sulphate. The solution is filtered and concentrated to dryness under reduced pressure (2.7 kPa). The oil obtained is chromatographed on a silica gel column (0.04 mm-0.06 mm, diameter 2.8 cm, height 26 cm), eluting under a nitrogen pressure of 0.6 bar with a cyclohexane and ethyl acetate mixture of (60/40 by volume) and collecting fractions of 60 cm 3 . Fractions 6 to 20 are pooled and concentrated to dryness under reduced pressure (2.7 kPa) and the residue is crystallized from an acetonitrile and diisopropyl oxide mixture. The crystals are drained and dried. 2.16 g of (4aRS,7aRS)-6-[(2-dimethylaminophenyl)acetyl]-4,4-diphenylperhydrothiopyrano[2,3-c]pyrrole are obtained in the form of a white solid; melting point 163° C.

Workup

  1. stirringThe reaction mixture is stirred for 1 hour at 20° C.
  2. washis then washed twice with 50 cm3 of water
  3. dry with materialdried over magnesium sulphate
  4. filtrationThe solution is filtered
  5. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  6. customThe oil obtained
  7. customis chromatographed on a silica gel column (0.04 mm-0.06 mm, diameter 2.8 cm, height 26 cm)
  8. washeluting under a nitrogen pressure of 0.6 bar
  9. additionwith a cyclohexane and ethyl acetate mixture of (60/40 by volume)
  10. customcollecting fractions of 60 cm 3
  11. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  12. customthe residue is crystallized from an acetonitrile and diisopropyl oxide mixture
  13. customdried

Sources & evidence

ORD record
ord-4dd01b6958d049949ec91cc243ca44b2
Source dataset
uspto-grants-1996_01
Patent number
US05484942

Linked notes

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