Hydrochloric Acid → HCID 13910656, compound

HRID 543438Notes

Reaction equation

HRID 543438 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][NH:13][CH2:14][CH2:15][C:16]2[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[CH:18][C:17]=2[C:24]#[C:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C=O.[C:34]([BH3-])#N.[Na+].Cl.[C:39]([OH:46])(=[O:45])/[CH:40]=[CH:41]/[C:42]([OH:44])=[O:43]>CO.CC(O)C>[C:39]([OH:46])(=[O:45])/[CH:40]=[CH:41]/[C:42]([OH:44])=[O:43].[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][N:13]([CH3:34])[CH2:14][CH2:15][C:16]2[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[CH:18][C:17]=2[C:24]#[C:25][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 444972Fumaric AcidHCID 5003444Sodium cyanoborohydrideHCID 13910651HCID 13910651, compound

Product 1

HCID 13910656HCID 13910656, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3776IsopropanolSolvent

Procedure

A solution of 1.7 g (4.09 mmole) of N-[2-(3,4-dimethoxyphenyl)ethyl]-5-methoxy-2-(phenylethynyl)benzeneethanamine in 30 ml of methanol was treated with 0.85 ml (10.2 mmole) of 37% aqueous formaldehyde solution and 0.95 g (15.1 mmole) of sodium cyanoborohydride. The mixture was stirred under an atmosphere of nitrogen for six hours, methanolic hydrogen chloride was added to pH 1, and the mixture stirred overnight at room temperature. The solvent was evaporated in vacuo and the residue partitioned between 3N sodium hydroxide and ether. The organic phase was separated, washed with brine, dried over anhydrous potassium carbonate and evaporated in vacuo to yield crude free base of the product. The free base was combined with one equivalent of fumaric acid in 2-propanol and allowed to crystallize overnight with cooling. Filtering afforded 1.73 g of nearly pure product which was recrystallized from a mixture of 95% ethanol and 2-propanol to yield pure N-[2-(3,4-dimethoxyphenyl)ethyl]-5-methoxy-N-methyl-2-(phenylethynyl)benzeneethanamine (E)-2-butenedioate (1:1 ), mp 152.5°-154° C.

Workup

  1. stirringthe mixture stirred overnight at room temperature
  2. customThe solvent was evaporated in vacuo
  3. customthe residue partitioned between 3N sodium hydroxide and ether
  4. customThe organic phase was separated
  5. washwashed with brine
  6. dry with materialdried over anhydrous potassium carbonate
  7. customevaporated in vacuo
  8. customto yield crude free base of the product
  9. customto crystallize overnight
  10. temperaturewith cooling
  11. filtrationFiltering
  12. customafforded 1.73 g of nearly pure product which
  13. customwas recrystallized from a mixture of 95% ethanol and 2-propanol

Sources & evidence

ORD record
ord-277a047146624ad0838983a44f91c0b0
Source dataset
uspto-grants-1987_04
Patent number
US04661635

Reaction notes

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