Acrylonitrile → HCID 13577178, compound

HRID 746162Notes

Reaction equation

HRID 746162 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][NH:6][C:7](=[O:15])[CH:8]([CH:10]([C:12]([OH:14])=[O:13])[OH:11])[OH:9].C(N(CC)CC)C.[C:23](#[N:26])[CH:24]=[CH2:25]>O>[C:23]([CH2:24][CH2:25][NH:1][CH2:2][CH2:3][CH2:4][CH2:5][NH:6][C:7](=[O:15])[CH:8]([CH:10]([C:12]([OH:14])=[O:13])[OH:11])[OH:9])#[N:26]

Participants

5

Reactant 3

HCID 7855AcrylonitrileHCID 8471TriethylamineHCID 13577176HCID 13577176, compound

Product 1

HCID 13577178HCID 13577178, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2.01 Grams (9.127 mmoles) of N-(4-aminobutyl)tartaric acid monoamide (IX) obtained in 1. was dissolved in 40 ml of water, and after adding 1.273 ml of triethylamine and then 0.726 ml of acrylonitrile, the resulting mixture was stirred for 27 hours at room temperature. The reaction solution was then dried to solid under reduced pressure. After adding 20 ml of water to the residual solid, the resulting solution was passed through a column packed with 300 ml of Dowex® 1×4(OH-), and after washing with 1.2 liters of water, eluted with 0.5N aqueous acetic acid solution. The fractions containing the objective compound were collected and concentrated under reduced pressure to obtain 2.235 g of a syrup-form N-[4-(2-cyanoethyl)aminobutyl]tartaric acid monoamide (XI) (yield, 89.6%).

Workup

  1. customThe reaction solution was then dried to solid under reduced pressure
  2. additionAfter adding 20 ml of water to the residual solid
  3. washafter washing with 1.2 liters of water
  4. washeluted with 0.5N aqueous acetic acid solution
  5. additionThe fractions containing the objective compound
  6. customwere collected
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d8bc654f4f0445a0be43321e98eb6247
Source dataset
uspto-grants-1986_07
Patent number
US04603015

Reaction notes

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