Dodecanoyl chloride → Dodecanoic acid, 2-(dimethylamino)-1-methylethyl ester

HRID 2227561Notes

Reaction equation

HRID 2227561 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].C(N(CC)CC)C.[CH3:22][N:23]([CH2:25][CH:26]([OH:28])[CH3:27])[CH3:24]>C(Cl)(Cl)Cl>[C:1]([O:28][CH:26]([CH3:27])[CH2:25][N:23]([CH3:24])[CH3:22])(=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

5

Reactant 3

HCID 8166Dodecanoyl chloride2×HCID 8471Triethylamine2×HCID 37511Dimepranol

Product 1

HCID 157516Dodecanoic acid, 2-(dimethylamino)-1-methylethyl ester

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

The foregoing (N-substituted amino)- and (N,N-disubstituted amino)-alkanol alkanoates are readily prepared by reacting the corresponding aminoalkanol with lauroyl chloride in the presence of triethylamine. A solvent such as chloroform is optional but preferred. For example, 1-(N,N-dimethylamino)-2-propanol can be reacted with lauroyl chloride in chloroform and in the presence of triethylamine to form 1-(N,N-dimethylamino)-2-propanol dodecanoate (DAIPD).

Sources & evidence

ORD record
ord-a4d39e2ca62947889726f235831eb036
Source dataset
uspto-grants-2002_07
Patent number
US06414028B1

Reaction notes

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