Hydrochloric Acid → HCID 13012191, compound

HRID 1710048Notes

Reaction equation

HRID 1710048 reaction equation
[NH2:1][C:2]1[N:3]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:4]2[CH2:5][CH2:6][CH2:7][CH2:8][C:9]=2[C:10]=1[C:11]#[N:12].[C:20]([O:26][CH2:27][CH3:28])(=[O:25])[CH2:21][C:22]([CH3:24])=O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[O-]CC.[Na+].Cl>C1(C)C=CC=CC=1.C(O)C.O>[NH2:12][C:11]1[C:10]2[C:9]3[CH2:8][CH2:7][CH2:6][CH2:5][C:4]=3[N:3]([CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:2]=2[N:1]=[C:22]([CH3:24])[C:21]=1[C:20]([O:26][CH2:27][CH3:28])=[O:25]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 6101p-Toluenesulfonic acidHCID 8868Ethyl AcetoacetateHCID 2723922Sodium ethoxideHCID 130121792-Amino-1-benzyl-4,5,6,7-tetrahydro-1H-indole-3-carbonitrile

Product 1

HCID 13012191HCID 13012191, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

The title compound was prepared using a modified procedure (see below) to that described by H. J. Roth et al., Arch. Pharmaz., 1976, 309, 597. 2-Amino-1-benzyl-3-cyano-4,5,6,7-tetrahydroindole (D1) (1.255 g; 5 mM) was added to a solution of ethyl acetoacetate (0.655 g; 5 mM) in toluene (60 ml) containing para-toluenesulphonic acid (30 mg), and the mixture refluxed vigorously for 1 h with water separation (Dean and Stark apparatus). To the cooled solution was then added 1M sodium ethoxide in ethanol (6 ml) and the mixture refluxed for a further 2 h. The cooled solution was poured onto water, and the pH of the stirred mixture adjusted to 7 using 5M hydrochloric acid. The toluene layer was then separated, and the aqueous phase re-extracted with toluene. The combined organic phase was washed with brine, dried and evaporated to give a brown oil (1.5 g). Crystallisation from ethanol afforded the title compound as off-white needles (0.8 g; 44%), m.p. 145.5° -147°.

Workup

  1. temperaturethe mixture refluxed for a further 2 h
  2. additionThe cooled solution was poured onto water
  3. customThe toluene layer was then separated
  4. extractionthe aqueous phase re-extracted with toluene
  5. washThe combined organic phase was washed with brine
  6. customdried
  7. customevaporated

Sources & evidence

ORD record
ord-b7e3cef5087740eea4ade781d9358905
Source dataset
uspto-grants-1990_08
Patent number
US04952584

Reaction notes

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