Propylamine → HCID 53679128, compound

HRID 398802Notes

Reaction equation

HRID 398802 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12](=[O:13])[C:11]3[CH2:14][CH2:15][CH2:16][CH2:17][C:10]=3[C:9]2=[O:18])=[CH:4][C:3]=1[CH:19]=[C:20](Cl)[CH:21]=C=O.[CH2:25]([NH2:28])[CH2:26][CH3:27]>C(OCC)(=O)C>[CH2:25]([NH:28][C:12](=[O:13])[C:11]1[CH2:14][CH2:15][CH2:16][CH2:17][C:10]=1[C:9]([NH:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([CH:19]=[C:20]([C:9](=[O:18])[NH:8][CH2:5][CH2:4][CH3:3])[CH3:21])[CH:4]=1)=[O:18])[CH2:26][CH3:27]

Participants

4

Reactant 2

HCID 7852PropylamineHCID 86753186HCID 86753186, compound

Product 1

HCID 53679128HCID 53679128, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
20 °C

Procedure

A solution of 10.9 g of N-[4-chloro-3-(2-chloro-carbonylprop-1-en-1-yl)-phenyl]-3,4,5,6-tetrahydrophthalimide in 200 ml of ethyl acetate was added dropwise to a solution of 5.9 g of n-propylamine in about 150 ml of ethyl acetate while cooling with ice. The mixture was stirred for 3 hours at about 20° C., after which the solid formed was separated off, washed twice with 5% by weight aqueous hydrochloric acid and then once with petroleum ether and then dried under reduced pressure at 40° C. The crude product was recrystallized from ethyl acetate. Mp.: 130°131° C.

Workup

  1. temperaturewhile cooling with ice
  2. customafter which the solid formed
  3. customwas separated off
  4. washwashed twice with 5% by weight aqueous hydrochloric acid
  5. dry with materialonce with petroleum ether and then dried under reduced pressure at 40° C
  6. customThe crude product was recrystallized from ethyl acetate
  7. custom130°131° C.

Sources & evidence

ORD record
ord-d2f90013b4ca45ccb1f2e24b4e32b75c
Source dataset
uspto-grants-1998_10
Patent number
US05817603

Reaction notes

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