Dodecanoyl chloride → N,N-Diethyl-N'-Dodecanoyl-1,3-Propylenediamine
Reaction equation
[C:1](Cl)(=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[CH2:15]([N:17]([CH2:22][CH3:23])[CH2:18][CH2:19][CH2:20][NH2:21])[CH3:16]>C(Cl)(Cl)Cl>[CH2:15]([N:17]([CH2:22][CH3:23])[CH2:18][CH2:19][CH2:20][NH:21][C:1](=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[CH3:16]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A 500 ml RB flask containing a solution of lauroyl chloride (19.03 g., 87 mM) in dry chloroform (200 ml) was cooled to 0° C. on an ice bath. A solution of N, N-diethly-1,3-propanediamine (15.00 g., 115 mM) in dry chloroform (25 ml) was added dropwise to the cold solution then allowed to warm to room temperature and stirred for 2 hours. The chloroform was removed under reduced pressure and the residue redissolved in an ethanol/water mixture (1:1) and neutralized with sodium bicarbonate, followed by extraction with chloroform (4×50 ml). The combined extracts were dried (MgSO4), concentrated, and the residue distilled under reduced pressure (bp 176° C., 20μ) to give 21.47 g. (79%) of the subject compound as an amber oil.
Workup
- temperatureto warm to room temperature
- customThe chloroform was removed under reduced pressure
- dissolutionthe residue redissolved in an ethanol/water mixture (1:1)
- extractionfollowed by extraction with chloroform (4×50 ml)
- dry with materialThe combined extracts were dried (MgSO4)
- concentrationconcentrated
- distillationthe residue distilled under reduced pressure (bp 176° C., 20μ)
- customto give 21.47 g
Sources & evidence
- ORD record
- ord-a75360fb98e348129d0138b29fd189fe
- Source dataset
- uspto-grants-1995_02
- Patent number
- US05393491
Reaction notes
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