Water → 7,8-Difluoro-1,2,3,4-tetrahydrocyclopent[b]indol-4-yl2-propylamine fumarate

HRID 49424Notes

Reaction equation

HRID 49424 reaction equation
Br[C:2]1[CH:8]=[C:7]([F:9])[C:6]([F:10])=[CH:5][C:3]=1[NH2:4].[C:11](=[O:14])([O-:13])[O-].[Na+].[Na+].F[C:18](F)(F)[C:19]([O:21][C:22](=O)[C:23](F)(F)F)=[O:20].O>CCOCC>[C:19]([OH:21])(=[O:20])/[CH:18]=[CH:2]/[C:11]([OH:13])=[O:14].[F:9][C:7]1[CH:8]=[CH:2][C:3]2[N:4]([NH:4][CH:3]([CH3:5])[CH3:2])[C:6]3[CH2:7][CH2:8][CH2:22][C:23]=3[C:5]=2[C:6]=1[F:10]

Participants

6

Reactant 4

HCID 962WaterHCID 9845Trifluoroacetic anhydrideHCID 10340Sodium CarbonateHCID 112065582-Bromo-4,5-difluoroaniline

Product 1

HCID 867593847,8-Difluoro-1,2,3,4-tetrahydrocyclopent[b]indol-4-yl2-propylamine fumarateYield 238.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a stirred solution of 2-bromo-4,5-difluoroaniline [H. Ishikawa, T. Uno, H, Miyamoto, H. Hiraki, H. Tamaoka, M. Tominaga and K. Nakagawa, Chem. Pharm. Bull., 1990, 38(9), 2459-2462] (72 g, 34 mmol) in ether (50 mL) at 0° C. was added sodium carbonate (5.4 g, 44 mmol) and trifluoroacetic anhydride (6.2 mL, 44 mmol). The reaction mixture was stirred at room temperature for 1 h. Water (100 mL) was added and the mixture was extracted with dichloromethane (3×100 mL). The organic extracts were combined, dried (magnesium sulfate), filtered and concentrated in vacuo to give the product (9.9 g, 94%) as a white solid. IR νmax (Nujol)/cm−1 3270, 1716, 1550, 1489, 1465, 1226, 1181, 919, 876 and 821; NMR δH (400 MHz, CDCl3) 7.45-7.5 (1H, dd, J 7.5 Hz), 8.28-8.34 (1H, dd, J 8 Hz) and 8.36 (1H, br s).

Workup

  1. extractionthe mixture was extracted with dichloromethane (3×100 mL)
  2. dry with materialdried (magnesium sulfate)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1a8bbcaf68f44b819ee9104b64462c13
Source dataset
uspto-grants-2004_03
Patent number
US06706750B1

Reaction notes

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