Methyl acetoacetate → 4-(2-hydroxyhexadecyl)aminoethyl-7-methyl-3,6-dihydro-2H-1,4-diazepin-5-one

HRID 67672

Reaction equation

[OH:1][CH:2]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:3][NH:4][CH2:5][CH2:6][NH:7][CH2:8][CH2:9][NH2:10].[C:25](OC)(=[O:30])[CH2:26][C:27]([CH3:29])=O>>[OH:1][CH:2]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:3][NH:4][CH2:5][CH2:6][N:7]1[C:25](=[O:30])[CH2:26][C:27]([CH3:29])=[N:10][CH2:9][CH2:8]1

Participants

Reactant 2

HCID 7757Methyl acetoacetate

HCID 201483611-({2-[(2-Aminoethyl)amino]ethyl}amino)hexadecan-2-OL

Product 1

HCID 131465184-(2-hydroxyhexadecyl)aminoethyl-7-methyl-3,6-dihydro-2H-1,4-diazepin-5-one

Procedure

Into an apparatus similar to that in Example 1, were charged 339.5 g (1 mole) of N-(2-hydroxy)hexadecyldiethylenetriamine and 116.1 g (1 mole) of methyl acetoacetate. At 140° to 150° C., 18 g of water and 32 g of methanol were distilled off to obtain 4-(2-hydroxyhexadecyl)aminoethyl-7-methyl-3,6-dihydro-2H-1,4-diazepin-5-one.

Workup

distillationAt 140° to 150° C., 18 g of water and 32 g of methanol were distilled off

Sources & evidence

ORD record: ord-8c8a17961a7d430590225145e3158f5e
Source dataset: uspto-grants-1982_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04346087

Linked notes

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