Hydrochloric Acid → HCID 15107537, compound

HRID 1090479Notes

Reaction equation

HRID 1090479 reaction equation
[CH3:1][NH:2][C:3]12[CH2:11][CH2:10][CH2:9][CH2:8]C1O[C:5]1[CH:12]=[CH:13][CH:14]=[CH:15][C:4]2=1.[C:16](OC(=O)C)(=[O:18])[CH3:17].Cl.[C:24](=[O:27])(O)[O-].[Na+]>C(Cl)Cl>[C:16]([N:2]([CH3:1])[C:3]12[CH2:11][CH2:10][CH2:9][CH2:8][CH:24]1[O:27][C:15]1[CH:14]=[CH:13][CH:12]=[CH:5][C:4]2=1)(=[O:18])[CH3:17]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 15107536HCID 15107536, compound

Product 1

HCID 15107537HCID 15107537, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

General procedure: A reaction mixture prepared from 8.5 g of N-methyl-6,7,8,9-tetrahydro-9a(5aH)-dibenzofuranamine, 50 ml of methylene dichloride and 4.8 g of acetic anhydride is allowed to stand at room temperature for 18 hours. The mixture is washed with one equivalent of 3 N hydrochloric acid, then with dilute sodium bicarbonate solution until slightly basic. The dried methylene chloride phase is evaporated to yield a residue of N-acetyl-N-methyl-6,7,8,9-tetrahydro-9a(5aH)-dibenzofuranamine. A solution of this residue in 30 ml of anhydrous ether is gradually added to a stirred solution of 5 g of lithium aluminum hydride in 400 ml of anhydrous ether. The mixture is stirred for 18 hours and then decomposed by the successive addition of 5 ml of water, 3.75 ml of 20% sodium hydroxide solution, and 7.5 ml water. The mixture is filtered and a slight excess of hydrogen chloride in isopropyl alcohol is added to the filtrate. The precipitated N-ethyl-N-methyl-6,7,8,9-tetrahydro-9a(SaH)-dibenzofuranamine hydrochloride is recrystallized from a mixture of methanol and ether, thereby yielding a material with mp about 138° C. to 139° C. The free base is obtained by treating an aqueous solution of the hydrochloride with sodium hydroxide and extracting with ether. A citrate is obtained by adding a solution of citric acid in methanol to a solution of the free base in methanol and concentrating.

Workup

  1. customThe dried methylene chloride phase is evaporated

Sources & evidence

ORD record
ord-b90f39617bf844d0a3eb0224bdc649da
Source dataset
uspto-grants-1992_01
Patent number
US05081304

Reaction notes

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