Water → HCID 9803779, compound

HRID 2307856Notes

Reaction equation

HRID 2307856 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([C:17]([NH:19][CH3:20])=O)=[CH:14][CH:15]=3)[C:10]([CH:21]3[CH2:26][CH2:25][N:24]([CH2:27][CH2:28][N:29]4[CH2:33][CH2:32][NH:31][C:30]4=[O:34])[CH2:23][CH2:22]3)=[CH:9]2)=[CH:4][CH:3]=1.O.[OH-].[Na+]>C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([CH2:17][NH:19][CH3:20])=[CH:14][CH:15]=3)[C:10]([CH:21]3[CH2:22][CH2:23][N:24]([CH2:27][CH2:28][N:29]4[CH2:33][CH2:32][NH:31][C:30]4=[O:34])[CH2:25][CH2:26]3)=[CH:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 9934107HCID 9934107, compound

Product 1

HCID 9803779HCID 9803779, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

1-(4-Fluorophenyl)-3-[1-[2-(2-imidazolidinon-1-yl)ethyl]4-piperidinyl]-N-methyl-1H-indole-5-carboxamide (7a) (2g) and LiAIH4 was refluxed in dry THF (150 mL) for 3 h. After cooling to 0° C., water (100 mL) and aqueous NaOH (1 M, 5 mL) was carefully added. The phases were separated and the aqueous phase was extracted with ethyl acetate. After removal of the solvent, the compound was purified by flash chromatography (EtOAc/MeOH/TEA 80/15/5). Yield 0.3 g (oil). 1H-NMR (DMSO) 1.72 (q, 2H), 1.97 (d, 2H), 2.12 (t, 2H), 2.28 (s, 3H), 2.45 (t, 2H), 2.77 (tt, 1H), 3.00 (d. 2H), 3.10-3.60 (m, 6H) 3.72 (s, 2H), 6.25 (s, 2H), 7.14 (d. 1H), 7.35-7.45 (m, 4H), 7.55-7.65 (m, 3H)

Workup

  1. customThe phases were separated
  2. extractionthe aqueous phase was extracted with ethyl acetate
  3. customAfter removal of the solvent
  4. customthe compound was purified by flash chromatography (EtOAc/MeOH/TEA 80/15/5)

Sources & evidence

ORD record
ord-f12084c17ae447c097d59121ff52ac34
Source dataset
uspto-grants-2004_12
Patent number
US06833376B2

Reaction notes

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