Hexamethylenediamine → N,N'-(1,6-hexylene)-bis[2-hydroxynonylamine]

HRID 1111896Notes

Reaction equation

HRID 1111896 reaction equation
[CH2:1]1[O:10][CH:2]1[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].[NH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][NH2:18]>C(O)C>[CH2:17]([NH:18][CH2:1][CH:2]([OH:10])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][NH:11][CH2:1][CH:2]([OH:10])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]

Participants

4

Reactant 2

HCID 16402HexamethylenediamineHCID 5511812-Heptyloxirane

Product 1

HCID 21332345N,N'-(1,6-hexylene)-bis[2-hydroxynonylamine]

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a manner similar to that of Example 1, condensation of 1-nonene oxide (97.4 g.) and hexamethylenediamine (39.8 g.) and recrystallization of the resulting product (67 g.) from ethanol afforded N,N'-(1,6-hexylene)-bis[2-hydroxynonylamine] (I: R = CH3 (CH2)6, R' = H, X = (CH2)6, Z = H) (67 g., m.p. 122°-129.2° C.).

Sources & evidence

ORD record
ord-945ac133103e46629044a1fb6f51bf6b
Source dataset
uspto-grants-1978_10
Patent number
US04119668

Reaction notes

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