Acetic Acid → HCID 22624482, compound

HRID 279225Notes

Reaction equation

HRID 279225 reaction equation
C([C:6]1[N:7]([CH2:15][CH2:16][CH2:17][NH:18]C(C2C3C(=CC=CC=3)C(=O)O2)=O)[C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2)(OCC)=O.[BH4-].[Na+].[C:33]([OH:36])(=[O:35])C.[CH:37](O)(C)[CH3:38]>O>[C:33]([C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:8]=1[N:7]([CH2:15][CH2:16][CH2:17][NH2:18])[CH:6]=[CH:14]2)([O:36][CH2:37][CH3:38])=[O:35]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 3776IsopropanolHCID 4311764Sodium borohydrideHCID 22624486HCID 22624486, compound

Product 1

HCID 22624482HCID 22624482, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 0.93 g (2.5 mmol) of carboethoxy-N-(3-phthalidamidopropyl)indole in 21 mL of isopropanol and 3.5 mL of water was added 0.47 g (12 mmol) of NaBH4 and the reaction mixture was stirred overnight at rt. To the reaction mixture was carefully added 2.4 mL of glacial acetic acid and the reaction mixture was heated at reflux for 24 h. The reaction mixture was concentrated and the residue was partitioned between EtOAc and 2N HCl. The aqueous layer was made basic with solid K2CO3 and extracted with EtOAc. The combined organic fractions were washed with sat'd NaCl solution, dried over Na2SO4, filtered and the filtrate was concentrated to give 0.57 g of 7-carboethoxy-N-(3-aminopropyl)indole that was used without further purification.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 24 h
  3. concentrationThe reaction mixture was concentrated
  4. customthe residue was partitioned between EtOAc and 2N HCl
  5. extractionextracted with EtOAc
  6. washThe combined organic fractions were washed with sat'd NaCl solution
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-77fbbfc4a9394d708d7b902b73bf0eb3
Source dataset
uspto-grants-2002_03
Patent number
US06362201B1

Reaction notes

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