Hydrochloric Acid → HCID 9859833, compound

HRID 1825718Notes

Reaction equation

HRID 1825718 reaction equation
O=[C:2]1[CH2:6][CH2:5][CH:4]([C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:16]#[N:17])[CH:14]=3)[NH:9][CH:8]=2)[CH2:3]1.[CH3:18][NH:19][CH3:20].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].Cl.C(=O)([O-])[O-].[Na+].[Na+]>CCO.O>[CH3:18][N:19]([CH3:20])[CH:2]1[CH2:6][CH2:5][CH:4]([C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:16]#[N:17])[CH:14]=3)[NH:9][CH:8]=2)[CH2:3]1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 674DimethylamineHCID 10340Sodium CarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 22139459HCID 22139459, compound

Product 1

HCID 9859833HCID 9859833, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

3-(3-oxocyclopentyl)-1H-indole-5-carbonitrile (2.24 g, 10 mMol) and dimethylamine (2.0 M solution in THF, 50 mL, 100 mMol) were dissolved in EtOH (150 mL). After stirring for 15 min, sodium triacetoxyborohydride (8.50 g, 40 mMol) was added and the reaction stirred for 4 h. The reaction was then diluted with water (100 mL) and made acidic (pH 3) with HCl (6 M). The reaction was then adjusted to pH 10 with sodium carbonate. It was extracted three times with ethyl acetate (100 mL) and the organic extracts were dried over sodium sulfate, concentrated in vacuo, and dried under high vacuum to give 3-(3-dimethylaminocyclopentyl)-1H-indole-5-carbonitrile (Compound 3, 2.5 g, 100%) as mixture of cis/trans diastereomers. 1H NMR (500 MHz, d4-MeOH) δ 8.02 (0.7 H s), 7.99 (0.3 H, s), 7.46 (0.4 H, s), 7.44 (0.6 H, s), 7.35 (1 H, dd, J=8.55 1.53), 7.24 (0.7 H, s), 7.21 (0.3 H, s), 3.49 (0.4 H, m), 3.37 (0.6 H, m), 2.92 (0.3 H, m), 2.83 (0.7 H, m), 2.41 (0.7 H, m), 2.36 (6 H, s), 2.22 (1.3 H, m), 2.07 (1 H, m), 1.80 (2 H, m), 1.67 (1 H, m). MS m/e 254.2 (M+H)+, 252.2 (M−H)+. LCMS (YMC ODS-A C18 S7 3.0×50 mm) tR, 0.857 min., MH+ 254.19.

Workup

  1. stirringthe reaction stirred for 4 h
  2. extractionIt was extracted three times with ethyl acetate (100 mL)
  3. dry with materialthe organic extracts were dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-8af91ecf23c34be0a689dc47cd1c459a
Source dataset
uspto-grants-2006_05
Patent number
US07049314B2

Reaction notes

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