1,2-Epoxybutane → 1-(2'-Hydroxybutyl)-2,2,4-trimethyl decahydroquinoline

HRID 616237Notes

Reaction equation

HRID 616237 reaction equation
[CH3:1][C:2]1([CH3:13])[CH2:11][CH:10]([CH3:12])[CH:9]2[CH:4]([CH2:5][CH2:6][CH2:7][CH2:8]2)[NH:3]1.[O:14]1[CH:16]([CH2:17][CH3:18])[CH2:15]1>C(O)C>[OH:14][CH:16]([CH2:17][CH3:18])[CH2:15][N:3]1[CH:4]2[CH:9]([CH2:8][CH2:7][CH2:6][CH2:5]2)[CH:10]([CH3:12])[CH2:11][C:2]1([CH3:13])[CH3:1]

Participants

4

Reactant 2

HCID 78341,2-EpoxybutaneHCID 226287862,2,4-Trimethyldecahydroquinoline

Product 1

HCID 205430911-(2'-Hydroxybutyl)-2,2,4-trimethyl decahydroquinoline

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Following the procedures given above, 2,2,4-trimethyl decahydroquinoline of about 76% cis structure was reacted with 1,2-epoxybutane in the presence of ethanol to yield 58 grams of 1-(2'-hydroxybutyl)-2,2,4-trimethyl decahydroquinoline, which had a boiling point of 110° - 112° C. at 0.50 mm Hg. Calculated contents for the formula C16H31NO were 75.83% carbon, 12.33% hydrogen, and 5.53% nitrogen and the measured values were 76.55% carbon, 13.13% hydrogen, and 5.49% nitrogen.

Sources & evidence

ORD record
ord-e70c52a4984c4f98a9568d029bb9c0b9
Source dataset
uspto-grants-1978_02
Patent number
US04073770

Reaction notes

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