Sodium borohydride → HCID 19079068, compound

HRID 1735860Notes

Reaction equation

HRID 1735860 reaction equation
[CH2:1]([C:4]1([C:19]#[N:20])[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[CH2:8][CH2:7][C:6]2[CH:15]=[CH:16][CH:17]=[CH:18][C:5]1=2)[CH:2]=[CH2:3].[BH4-].[Na+]>[Co](Cl)Cl.C(O)C>[CH2:1]([C:4]1([CH2:19][NH2:20])[C:5]2[CH:18]=[CH:17][CH:16]=[CH:15][C:6]=2[CH2:7][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]1=2)[CH2:2][CH3:3]

Participants

5

Reactant 2

HCID 4311764Sodium borohydride2×HCID 19079046HCID 19079046, compound

Product 1

HCID 19079068HCID 19079068, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 24288Cobalt(II) chlorideCatalystHCID 702EthanolSolvent

Procedure

Dissolved 10,11-dihydro-5-(2-propenyl)-5H-dibenzo[a,d]cyclohepten-5-nitrile (4.68 g, 0.018 mol) is 150 mL of absolute ethanol, and added sodium borohydride (1.70 g, 0.045 mol). Stirred at room temperature for 15 mins then cooled to 0° C. Added cobalt (II) chloride (4.29 g, 0.018 mol) portionwise. Stirred at room temperature for 30 mins then added additional sodium borohydride (1.70 g, 0.045 mol). Stirred at room temperature for 16 hours. Evaporated, and added 0.5N HCl. Washed with ethyl acetate, and extracted organic solution with 1.0N HCl. Combined acidic aqueous extracts, and made basic with 25 weight % NaOH. Extracted basic solution with dichloromethane. Dried combined organic extracts with MgSO4, filtered, and evaporated. Purified by flash chromatography on silica gel eluting with ethyl acetate. Combined appropriate fractions, and evaporated to give 1.4 g (30% yield) of 10,11-dihydro-5-propyl-5H-dibenzo[a,d]cycloheptene-5-methanamine as an oil. Dissolved free base in ethyl acetate, and added one equivalent of maleic acid dissolved in ethanol. Added ether to precipitate maleate salt.

Workup

  1. temperaturethen cooled to 0° C
  2. stirringStirred at room temperature for 30 mins
  3. stirringStirred at room temperature for 16 hours
  4. customEvaporated
  5. additionadded 0.5N HCl
  6. washWashed with ethyl acetate
  7. extractionextracted organic solution with 1.0N HCl
  8. extractionExtracted basic solution with dichloromethane
  9. customDried
  10. filtrationfiltered
  11. customevaporated
  12. customPurified by flash chromatography on silica gel eluting with ethyl acetate
  13. customevaporated

Sources & evidence

ORD record
ord-327fce5ca27e4c7ba02d85e69542a15e
Source dataset
uspto-grants-1996_07
Patent number
US05538986

Reaction notes

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