1-Pyrrolidineethanamine → HCID 68746920, compound

HRID 1864775Notes

Reaction equation

HRID 1864775 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[F:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[CH:23]=[C:24]3[C:28](=[CH:29][CH:30]=2)[NH:27][CH:26]=[CH:25]3)=[CH:18][C:17]=1[CH:31]=O.[NH2:33][CH2:34][CH2:35][N:36]1[CH2:40][CH2:39][CH2:38][CH2:37]1.C(=O)(O)[O-].[Na+]>ClCCCl.ClCCl.C(O)(=O)C>[F:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[CH:23]=[C:24]3[C:28](=[CH:29][CH:30]=2)[NH:27][CH:26]=[CH:25]3)=[CH:18][C:17]=1[CH2:31][NH:33][CH2:34][CH2:35][N:36]1[CH2:40][CH2:39][CH2:38][CH2:37]1

Participants

8

Reactant 4

HCID 13441-PyrrolidineethanamineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 86616466HCID 86616466, compound

Product 1

HCID 68746920HCID 68746920, compoundYield 31.8%

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

Sodium triacetoxyborohydride (530 g, 2.51 mmol) and then enough acetic acid to bring the pH to 5 were added to a solution of 5-(4-fluoro-3-formylphenyl)-1H-indole (200 mg, 0.84 mmol) and 1-(2-aminoethyl)pyrrolidine (191 mg, 1.67 mmol) in 15 mL of 1,2-dichloroethane. The mixture was stirred at ambient temperature overnight, and then it was diluted with dichloromethane, and neutralized with the careful addition of saturated sodium bicarbonate solution. The layers were separated and the aqueous phase extracted into dichloromethane. The combined organic phases were dried over magnesium sulfate, filtered and concentrated to leave the crude product. Chromatography (elution with methanol/dichloromethane) provided 90 mg of the title compound. LC/MS: Retention time, 0.34 min.

Workup

  1. customThe layers were separated
  2. extractionthe aqueous phase extracted into dichloromethane
  3. dry with materialThe combined organic phases were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto leave the crude product
  7. washChromatography (elution with methanol/dichloromethane)

Sources & evidence

ORD record
ord-bc37002e401345ea8f9a1c2fe043c5e5
Source dataset
uspto-grants-2009_12
Patent number
US07625889B2

Reaction notes

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