Hexamethylenediamine → N,N'-bis[3-(3,5-dicyclohexyl-4-hydroxyphenyl)propionyl]-1,6-diaminohexane

HRID 256102

Reaction equation

[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][NH2:8].[CH:9]1([C:15]2[CH:16]=[C:17]([CH2:28][CH2:29][C:30](OC)=[O:31])[CH:18]=[C:19]([CH:22]3[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]3)[C:20]=2[OH:21])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.[C:34](=[O:37])(O)[O-].[Na+]>C(O)(=O)C>[CH:22]1([C:19]2[CH:18]=[C:17]([CH2:28][CH2:29][C:30]([NH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][NH:8][C:34](=[O:37])[CH2:29][CH2:28][C:17]3[CH:18]=[C:19]([CH:22]4[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]4)[C:20]([OH:21])=[C:15]([CH:9]4[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]4)[CH:16]=3)=[O:31])[CH:16]=[C:15]([CH:9]3[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]3)[C:20]=2[OH:21])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

Conditions

Temperature: 175 °C

Procedure

11.6 of 1,6-diaminohexane are heated, under nitrogen, to 175° C. Then 0.2 g of acetic acid are added. Over 1 hour, 68.9 g of methyl 3-(3,5-dicyclohexyl-4-hydroxyphenyl)propionate are added to this mixture. The reaction mixture is heated for a further 3 hours at 175° C. The mixture is stirred, in a mixer, with 100 ml of 1% aqueous sodium bicarbonate. The resultant solid is isolated by suction filtration and washed with water until neutral. After drying, 60.3 g of a colourless powder with a melting point of 28° C. are obtained.

Workup

customThe resultant solid is isolated by suction filtration
washwashed with water until neutral
customAfter drying

Sources & evidence

ORD record: ord-2347a82685d14b7e83c81d4e7e5ff919
Source dataset: uspto-grants-1987_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04699939

Linked notes

Loading…