Tetrahydrofuran → HCID 67605379, compound

HRID 1735859Notes

Reaction equation

HRID 1735859 reaction equation
C([C:4]1([CH2:19][CH2:20][CH:21]=O)[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[CH2:8][CH2:7][C:6]2C=[CH:16][CH:17]=[CH:18][C:5]1=2)CC.Cl.[CH3:24][NH:25][CH3:26].C([BH3-])#N.[Na+].[CH2:31]1[CH2:35]O[CH2:33][CH2:32]1>CO>[CH3:24][N:25]([CH3:26])[CH2:33][CH2:32][CH2:31][C:35]1[C:6]2[CH2:7][CH2:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[CH:4]([CH2:19][CH2:20][CH3:21])[C:5]=2[CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 10473Dimethylamine, hydrochlorideHCID 5003444Sodium cyanoborohydrideHCID 19434455HCID 19434455, compound

Product 1

HCID 67605379HCID 67605379, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Dissolved 3-[10,11-dihydro-5-propyl-5H-dibenzo[a,d]cyclohepten-5yl]-propanal (0.75 g, 2.56 mmol) in 5 mL of dry THF and 10 mL of dry methanol. Added 3A sieves, dimethylamine hydrochloride (1.05 g, 12.82 mmol), and sodium cyanoborohydride (0.161 g, 2.56 mmol). Stirred to room temperature for 24 hours. Added saturated NaHCO3, and filtered through celite. Extracted filtrate 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 0.53 g (65% yield) of 10,11-dihydro-N,N-dimethyl-5-propyl-5H-dibenzo[a,d]cycloheptenepropanamine as an oil. Dissolved free base in dichloromethane, and added 28.8 weight % HCl-ethanol until acidic. Evaporated to give hydrochloride salt as a foam.

Workup

  1. filtrationAdded saturated NaHCO3, and filtered through celite
  2. customDried
  3. filtrationfiltered
  4. customevaporated
  5. customPurified crude product by flash chromatography on silica gel eluting with 3% MeOH
  6. customevaporated

Sources & evidence

ORD record
ord-ac5317493a334028b9c68b17291e84dd
Source dataset
uspto-grants-1996_07
Patent number
US05538986

Reaction notes

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