Sodium Bicarbonate → [2-(2-Chloro-4-nitrophenyl)ethyl]cyclopropylmethylamine

HRID 735126Notes

Reaction equation

HRID 735126 reaction equation
[CH3:1][NH:2]C1CC1.[Cl:6][C:7]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=[CH:9][C:8]=1[CH2:16][CH:17]=O.C(O[BH-](O[C:29](=O)[CH3:30])OC(=O)C)(=O)C.[Na+].[C:33](=O)([O-])O.[Na+]>C1COCC1>[Cl:6][C:7]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=[CH:9][C:8]=1[CH2:16][CH2:17][NH:2][CH2:1][CH:29]1[CH2:30][CH2:33]1

Participants

6

Reactant 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 11029756N-MethylcyclopropanamineHCID 54570839(2-Chloro-4-nitrophenyl)acetaldehyde

Product 1

HCID 68816321[2-(2-Chloro-4-nitrophenyl)ethyl]cyclopropylmethylamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.07 g (10 mmol) of N-methylcyclopropylamine is added to a solution of 1 g (5.01 mmol) of (2-chloro-4-nitrophenyl)acetaldehyde in 50 mL of THF and then 4.46 g (20 mmol) of sodium triacetoxyborohydride (95%) is added. The reaction mixture is stirred for 120 hours at ambient temperature and then poured into a saturated sodium hydrogen carbonate solution and twice extracted with ethyl acetate. The combined organic phases are dried over sodium sulfate. The purification is carried out by column chromatography on Alox, neutral, act. II-III (eluant: petroleum ether/ethyl acetate (5:1)). Yield: 0.75 g (58.8% of theory); C12H15ClN2O2 (M=254.71); calc.: molecular ion peak (M+H)+: 255/257; found: molecular ion peak (M+H)+: 255/257; Rf value: 0.61 (Alox, petroleum ether/ethyl acetate (5:1)).

Workup

  1. extractiontwice extracted with ethyl acetate
  2. dry with materialThe combined organic phases are dried over sodium sulfate
  3. customThe purification

Sources & evidence

ORD record
ord-f586cc0f227f44dd88d4834b8c933a21
Source dataset
uspto-grants-2009_09
Patent number
US07592373B2

Reaction notes

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