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

HRID 2249586Notes

Reaction equation

HRID 2249586 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-f1287c49bbe44340937598b58949b0e8
Source dataset
uspto-grants-2008_01
Patent number
US07314884B2

Reaction notes

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