Sodium Bicarbonate → HCID 23372181, compound

HRID 1900246Notes

Reaction equation

HRID 1900246 reaction equation
[CH:1]1[C:11]2[CH:10]([CH:12]([CH2:15][CH:16]=[CH2:17])[CH:13]=O)[C:9]3[CH:18]=[CH:19][CH:20]=[CH:21][C:8]=3[CH2:7][O:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.Cl.[CH3:23][NH2:24].C([BH3-])#N.[Na+].C([O-])(O)=O.[Na+]>C1COCC1.CO.ClCCl>[CH3:23][NH:24][CH2:13][CH:12]([CH:10]1[C:9]2[CH:18]=[CH:19][CH:20]=[CH:21][C:8]=2[CH2:7][O:6][C:5]2[CH:4]=[CH:3][CH:2]=[CH:1][C:11]1=2)[CH2:15][CH:16]=[CH2:17]

Participants

8

Reactant 4

HCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 6364545Methylamine hydrochlorideHCID 54347581HCID 54347581, compound

Product 1

HCID 23372181HCID 23372181, compoundYield 73%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Dissolved 2-[6,11 -dihydro-dibenzo[b,e]oxepin-11-yl]-pent-4-en-1-al (5.0 g, 18.0 mmol) in 20 mL of dry THF and 60 mL of dry MeOH. Added 3 A molecular sieves, methylamine hydrochloride (6.1 g, 89.8 mmol), and then sodium cyanoborohydride (1.13 g, 18.0 mmol). Stirred at room temperature for 23 hours. Evaporated reaction mixture. Added 80 mL of saturated NaHCO3 and 80 mL of dichloromethane. FIltered through celite. 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 5% MeOH--CH2Cl2. Combined appropriate fractions and evaporated to give 3.8 g (73% yield) of N-methyl-2-[6,11-dihydro-dibenzo[b,e]oxepin-11-yl]-pent-4-en-1-amine. Dissolved free base in ethyl acetate, and added one equivalent of maleic acid dissolved in ethanol. Evaporated to give maleate salt as a glass.

Workup

  1. customEvaporated
  2. customreaction mixture
  3. filtrationFIltered through celite
  4. customDried
  5. filtrationfiltered
  6. customevaporated
  7. customPurified crude product by flash chromatography on silica gel eluting with 5% MeOH
  8. customevaporated

Sources & evidence

ORD record
ord-bf90cdfa5f144cbf850323c8cbe68c9b
Source dataset
uspto-grants-1996_11
Patent number
US05574173

Reaction notes

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