Potassium Carbonate → HCID 19079066, compound

HRID 1735864Notes

Reaction equation

HRID 1735864 reaction equation
[CH2:1]([O:3][C:4]1([CH2:19][CH:20]=O)[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[CH2:8][O:7][C:6]2[CH:15]=[CH:16][CH:17]=[CH:18][C:5]1=2)[CH3:2].Cl.[NH:23]1[CH2:27][CH2:26][CH2:25][CH2:24]1.C([BH3-])#N.[Na+].C([O-])([O-])=O.[K+].[K+]>C1COCC1.CO.ClCCl>[CH2:1]([O:3][C:4]1([CH2:19][CH2:20][N:23]2[CH2:27][CH2:26][CH2:25][CH2:24]2)[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[CH2:8][O:7][C:6]2[CH:15]=[CH:16][CH:17]=[CH:18][C:5]1=2)[CH3:2]

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 212848Pyrrolidine, hydrochloride (1:1)HCID 5003444Sodium cyanoborohydrideHCID 19079048HCID 19079048, compound

Product 1

HCID 19079066HCID 19079066, compoundYield 35.2%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Dissolved 2-[6,11-dihydro-11-ethoxy-dibenz[b,e]oxepin-11-yl]-ethanal (500 mg, 1.77 mmol) in 2 mL of dry THF and 6 mL of dry methanol. Added 3 A sieves, pyrrolidine hydrochloride (952 mg, 8.85 mmol), and then sodium cyanoborohydride (111 mg, 1.77 mmol). Stirred at room temperature under a drying tube for 24 hours. Added 30 mL of saturated K2CO3 and 15 mL of dichloromethane. Filtered through celite, and separated layers. Extracted aqueous solution with dichloromethane. Dried combined organic extracts with MgSO4, filtered, and evaporated. Purified crude product by flash chromatography on silica gel eluting with 3% MeOH--CH2Cl2 then 10% MeOH--CH2Cl2. Combined appropriate fractions, and evaporated to give 0.21 g (35% yield) of 1-[2-(11-ethoxy-6,11-dihydrodibenz[b,e]oxepin-11-yl)ethyl]pyrrolidine as a colorless oil. Dissolved free base in ethyl acetate, and added one equivalent of maleic acid dissolved in ethanol. Evaporated, added ethyl acetate, and evaporated again. Added ether to precipitate maleate salt.

Workup

  1. filtrationFiltered through celite
  2. customseparated layers
  3. customDried
  4. filtrationfiltered
  5. customevaporated
  6. customPurified crude product by flash chromatography on silica gel eluting with 3% MeOH
  7. customevaporated

Sources & evidence

ORD record
ord-e41a6f85f6f546c1a06808147ce15398
Source dataset
uspto-grants-1996_07
Patent number
US05538986

Reaction notes

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