Water → 2-Amino-N-(1,1-dimethylhexyl)acetamide hydrogen fumarate

HRID 1277493Notes

Reaction equation

HRID 1277493 reaction equation
[CH3:1][C:2]([OH:9])([CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])[CH3:3].C=[N:11][CH2:12][C:13]#[N:14].[OH2:15].F[C:17](F)(F)[C:18]([OH:20])=[O:19]>>[C:18]([OH:20])(=[O:19])/[CH:17]=[CH:4]/[C:2]([OH:9])=[O:15].[NH2:11][CH2:12][C:13]([NH:14][C:2]([CH3:3])([CH3:1])[CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])=[O:19]

Participants

5

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 80152-(Methyleneamino)acetonitrileHCID 122422-Methyl-2-heptanol

Product 1

HCID 234541302-Amino-N-(1,1-dimethylhexyl)acetamide hydrogen fumarate

Conditions

Temperature
10 °C

Procedure

To a solution of 2-methylheptan-2-ol (6.50 g.; 0.05 mole) in trifluoroacetic acid (20 ml) at -5° C. was added powdered methyleneaminoacetonitrile (3.40 g.; 0.05 mole) over 10 minutes. The slurry was allowed to warm to 10° C. and stirred until homogeneous (2 hours). After an additional 2 hours at 10° C., the reaction mixture was poured into water (100 ml) and the neutral material extracted with ether. The acid solution was basified with ammonia (pH 9-10) and the liberated base extracted into ether (3×80 ml). The combined extractswere dried over Na2SO4, filtered, and evaporated to dryness to give a colourless oil which was converted to the hydrogen fumarate salt, m.p. 156°-158° C.

Workup

  1. waitAfter an additional 2 hours at 10° C.
  2. extractionthe neutral material extracted with ether
  3. extractionthe liberated base extracted into ether (3×80 ml)
  4. dry with materialThe combined extractswere dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customto give a colourless oil which

Sources & evidence

ORD record
ord-fbb3ebd3ca53498a90b9dace0ad8ae6c
Source dataset
uspto-grants-1981_07
Patent number
US04277498

Reaction notes

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