1-Butanol → HCID 13715336, compound

HRID 1607123Notes

Reaction equation

HRID 1607123 reaction equation
[C:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[O:12][CH2:13][CH:14]2[O:16][CH2:15]2)[NH:5][CH:4]=1)#[N:2].C(O)CCC.[O:22]([CH:26]([CH3:34])[CH2:27][C:28]([NH:30][CH2:31][CH2:32][NH2:33])=[O:29])[N+:23]([O-:25])=[O:24].[C:35]([OH:42])(=[O:41])/[CH:36]=[CH:37]/[C:38]([OH:40])=[O:39]>CO>[C:35]([OH:42])(=[O:41])/[CH:36]=[CH:37]/[C:38]([OH:40])=[O:39].[C:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[O:12][CH2:13][CH:14]([OH:16])[CH2:15][NH:33][CH2:32][CH2:31][NH:30][C:28](=[O:29])[CH2:27][CH:26]([O:22][N+:23]([O-:25])=[O:24])[CH3:34])[NH:5][CH:4]=1)#[N:2]

Participants

6

Reactant 4

HCID 2631-ButanolHCID 444972Fumaric AcidHCID 12798005HCID 12798005, compoundHCID 137153344-[(2-Aminoethyl)amino]-4-oxobutan-2-yl nitrate

Product 1

HCID 13715336HCID 13715336, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4.2 g. 1-(3-cyanoindol-4-yloxy)-2,3-epoxypropane (see European patent specification No. 0,045,910) are suspended in 100 ml. n-butanol, mixed with 11.5 g. 2-(3-nitroxybutanoylamino)-ethylamine and stirred for 2 days at ambient temperature. After removal of the solvent, the residue is chromatographed on silica gel with methylene chloride/methanol (95:5 v/v) and methylene chloride/methanolic ammonia solution (95:5 v/v). From the appropriate fractions, after removal of the solvent, there are obtained 4.6 g. of base. By dissolving in methanol and adding the calculated amount of fumaric acid, there are obtained, after suction filtration, 3.9 g. (40% of theory) of the desired fumarate; m.p. 155°-156° C.

Workup

  1. customAfter removal of the solvent
  2. customthe residue is chromatographed on silica gel with methylene chloride/methanol (95:5 v/v) and methylene chloride/methanolic ammonia solution (95:5 v/v)
  3. customFrom the appropriate fractions, after removal of the solvent, there
  4. customare obtained 4.6 g
  5. customare obtained
  6. filtrationafter suction filtration, 3.9 g

Sources & evidence

ORD record
ord-a959de38b0a8486eaf8ef1a28814a2d3
Source dataset
uspto-grants-1989_09
Patent number
US04863949

Reaction notes

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