Methanol → HCID 20319970, compound

HRID 866632Notes

Reaction equation

HRID 866632 reaction equation
[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]/[C:4]([OH:6])=[O:5].[CH3:9][NH:10][CH:11]1[CH2:17][CH2:16][C:15]2[CH:18]=[CH:19][CH:20]=[CH:21][C:14]=2[NH:13][CH2:12]1.CO>C(OCC)(=O)C>[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]/[C:4]([OH:6])=[O:5].[CH3:9][NH:10][CH:11]1[CH2:17][CH2:16][C:15]2[CH:18]=[CH:19][CH:20]=[CH:21][C:14]=2[NH:13][CH2:12]1.[CH3:9][NH:10][CH:11]1[CH2:17][CH2:16][C:15]2[CH:18]=[CH:19][CH:20]=[CH:21][C:14]=2[NH:13][CH2:12]1

Participants

5

Reactant 3

HCID 887Methanol2×HCID 444972Fumaric AcidHCID 20319967HCID 20319967, compound

Product 1

HCID 20319970HCID 20319970, compoundYield 82.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 247 mg of fumaric acid in 10 ml of methanol was added to a solution of 750 mg of N-methyl-2,3,4,5-tetrahydro-[1H]-1-benzazepine-3-amine in 30 ml of ethyl acetate and the mixture was concentrated under reduced pressure to 10 ml and was vacuum filtered to obtain 900 mg of raw product. The latter was dissolved in methanol and the solution was filtered. The filtrate was added to isopropanol and the mixture was concentrated until crystallization occured. The mixture was vacuum filtered to obtain 820 mg of di-[N-methyl-2,3,4,5-tetrahydro-[1H]-1-benzazepine-3-amine] fumarate in the form of colorless crystals melting at 190° C.

Workup

  1. concentrationthe mixture was concentrated under reduced pressure to 10 ml
  2. filtrationfiltered
  3. customto obtain 900 mg of raw product
  4. filtrationthe solution was filtered
  5. additionThe filtrate was added to isopropanol
  6. concentrationthe mixture was concentrated until crystallization
  7. filtrationfiltered

Sources & evidence

ORD record
ord-5c5dcecb76a841658838e1866e6ab2d9
Source dataset
uspto-grants-1978_07
Patent number
US04100278

Reaction notes

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