Hydrochloric Acid → (S)-2-(5-Cyano-indol-1-yl)-1-methyl-ethylamine

HRID 1716534Notes

Reaction equation

HRID 1716534 reaction equation
C(OC(=O)[NH:7][C@@H:8]([CH3:21])[CH2:9][N:10]1[C:18]2[C:13](=[CH:14][C:15]([C:19]#[N:20])=[CH:16][CH:17]=2)[CH:12]=[CH:11]1)(C)(C)C.Cl>C(OCC)(=O)C>[C:19]([C:15]1[CH:14]=[C:13]2[C:18](=[CH:17][CH:16]=1)[N:10]([CH2:9][C@@H:8]([NH2:7])[CH3:21])[CH:11]=[CH:12]2)#[N:20]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67031525(S)-[2-(5-Cyano-indol-1-yl)-1-methyl-ethyl]-carbamic Acid Tert-Butyl Ester

Product 1

HCID 67031616(S)-2-(5-Cyano-indol-1-yl)-1-methyl-ethylamine

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The product obtained in step A] (500 mg) was treated with 2.2M HCl in ethyl acetate (15 mL) at RT for 60 minutes. After complete consumption of the starting material, the reaction mixture was diluted with ethyl acetate, washed with saturated NaHCO3 solution and brine, dried, filtered and evaporated. The crude product was purified by flash chromatography using CH2Cl2/MeOH/NH4OH 95:5:0.5 as an eluent. The fractions containing pure product were combined and evaporated to give the title compound as a colorless oil (251 mg).

Workup

  1. customAfter complete consumption of the starting material
  2. additionthe reaction mixture was diluted with ethyl acetate
  3. washwashed with saturated NaHCO3 solution and brine
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude product was purified by flash chromatography
  8. additionThe fractions containing pure product
  9. customevaporated

Sources & evidence

ORD record
ord-5568f5d1cbf34fd09ba3e41c8cfa428d
Source dataset
uspto-grants-2010_09
Patent number
US07803819B2

Reaction notes

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