1-Nitropropane → N,N-dimethyl-2-(3-cyanoindol-5-yl)cycloprop-1-yl methylamine

HRID 2416254Notes

Reaction equation

HRID 2416254 reaction equation
[CH3:1][N:2]([CH2:4][CH:5]1[CH2:7][CH:6]1[C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][CH:12]=[C:11]2[CH:17]=O)[CH3:3].P([O-])([O-])(O)=O.[NH4+].[NH4+].[N+:26](CCC)([O-])=O.[OH-].[Na+]>C(O)(=O)C.O>[CH3:1][N:2]([CH2:4][CH:5]1[CH2:7][CH:6]1[C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][CH:12]=[C:11]2[C:17]#[N:26])[CH3:3]

Participants

7

Reactant 4

HCID 79031-NitropropaneHCID 14798Sodium HydroxideHCID 24540Diammonium hydrogen phosphateHCID 22638743N,N-dimethyl-2-(3-formyl-indol-5-yl)cycloprop-1-yl-methylamine

Product 1

HCID 22638784N,N-dimethyl-2-(3-cyanoindol-5-yl)cycloprop-1-yl methylamineYield 75.9%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

In 5 mL of acetic acid was combined 120 mg of crude N,N-dimethyl-2-(3-formyl-indol-5-yl)cycloprop-1-yl-methylamine, ammonium hydrogen phosphate (0.48 g, 3.62 mmol, 7.3 equiv.), and nitropropane (0.04 mL, 0.5 mmol, 1 equiv.). The mixture was stirred and heated to a gentle reflux for 16 h. Water was added after cooling reaction to room temperature, and the mixture was made basic by the addition of 1 N NaOH. The mixture was extracted with ethyl acetate and dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo to give N,N-dimethyl-2-(3-cyanoindol-5-yl)cycloprop-1-yl methylamine (90 mg, 75%) as a brown oil. The oil was purified by flash chromatography to give a brown solid with 92% purity by reverse-phase HPLC. 1H NMR (MeOH-d4): δ 7.88 (s, 1H), 7.40 (d, J=7.5 Hz, 1H), 7.36 (d, J=1.9 Hz, 1H), 7.04 (dd, J=8.5, 1.7 Hz, 1H), 2.62 (dd, J=7.3 Hz, 1H), 2.42 (m, 1H), 2.38 (s, 6H), 1.89 (m, 1H), 1.20 (m, 1H), 1.08 (m, 1H), and 0.90 (m, 1H). IR: 2214.5 cm−1. FIMS: 238.2 (M−H)−.

Workup

  1. temperatureheated to
  2. temperaturea gentle reflux for 16 h
  3. temperatureafter cooling
  4. customreaction to room temperature
  5. extractionThe mixture was extracted with ethyl acetate
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-aac6c1adb67a4494bd51de2405b9c463
Source dataset
uspto-grants-2004_11
Patent number
US06822100B2

Reaction notes

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