Formic Acid → 2-amino-3-(1H-indol-3-yl)-N-(2-methoxybenzyl)propanamide

HRID 865501Notes

Reaction equation

HRID 865501 reaction equation
C(O)=O.[NH:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([CH2:13][CH:14]([NH:27]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[C:15]([NH:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[O:25][CH3:26])=[O:16])=[CH:5]1>C(Cl)Cl>[NH:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([CH2:13][CH:14]([NH2:27])[C:15]([NH:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[O:25][CH3:26])=[O:16])=[CH:5]1

Participants

4

Reactant 2

HCID 284Formic AcidHCID 187096163-(1H-indol-3-yl)-N-(2-methoxybenzyl)-2-(N-triphenylmethylamino)propanamide

Product 1

HCID 108058582-amino-3-(1H-indol-3-yl)-N-(2-methoxybenzyl)propanamideYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Formic acid (9.0 ml, 238.540 mmol) was added to a stirring solution of 3-(1H-indol-3-yl)-N-(2-methoxybenzyl)-2-(N-triphenylmethylamino)propanamide (14.11 g, 23.763 mmol) in anhydrous methylene chloride under a nitrogen atmosphere at 0° C. After 4 hours, the reaction mixture was concentrated to an oil on a rotary evaporator and redissolved in diethyl ether and 1.0N hydrochloric acid. The aqueous layer was washed twice with diethyl ether and basified with sodium hydroxide to a pH greater than 12. The product was extracted out with methylene chloride (4×). The organic extracts were combined, dried over anhydrous sodium sulfate, filtered, and concentrated on a rotary evaporator to a white foam. The compound 3-(1H-indol-3-yl)-2-amino-N-(2-methoxybenzyl)propanamide (7.52 g, 21.397 mmols) was isolated giving a 90% yield. No further purification was necessary.

Workup

  1. concentrationthe reaction mixture was concentrated to an oil on a rotary evaporator
  2. dissolutionredissolved in diethyl ether
  3. washThe aqueous layer was washed twice with diethyl ether
  4. extractionThe product was extracted out with methylene chloride (4×)
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated on a rotary evaporator to a white foam

Sources & evidence

ORD record
ord-d741bb2b892e4101812447b07b0bed25
Source dataset
uspto-grants-1996_10
Patent number
US05565568

Reaction notes

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