N,N-Dimethyl-1,3-propanediamine → N-[3-(dimethylamino)propyl]-N'-hexadecylurea

HRID 621768Notes

Reaction equation

HRID 621768 reaction equation
[CH2:1]([N:17]=[C:18]=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[CH3:20][N:21]([CH3:26])[CH2:22][CH2:23][CH2:24][NH2:25]>O1CCCC1>[CH3:20][N:21]([CH3:26])[CH2:22][CH2:23][CH2:24][NH:25][C:18]([NH:17][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])=[O:19]

Participants

4

Reactant 2

HCID 7993N,N-Dimethyl-1,3-propanediamineHCID 74751Hexadecane, 1-isocyanato-

Product 1

HCID 14407598N-[3-(dimethylamino)propyl]-N'-hexadecylurea

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.34 ml (5 meq) of hexadecyl isocyanate and 0.7 ml (5 meq) of 3-dimethylaminopropylamine are combined in 5 ml of tetrahydrofuran and reacted over a weekend at room temperature. The reaction mixture is filtered, washed with tetrahydrofuran, dried in vacuo and recrystallized from acetone to yield 1.2 gm of title compound with a m.p. of 78°-79° C.

Workup

  1. customreacted over a weekend at room temperature
  2. filtrationThe reaction mixture is filtered
  3. washwashed with tetrahydrofuran
  4. customdried in vacuo
  5. customrecrystallized from acetone

Sources & evidence

ORD record
ord-4f0755bbb8ce46399751b5d23e0ed7fa
Source dataset
uspto-grants-1989_04
Patent number
US04824996

Reaction notes

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