Acetone → HCID 53687623, compound

HRID 2057872Notes

Reaction equation

[C:1](=[N:4][CH:5]=[CH:6][CH3:7])([CH3:3])[CH3:2].[CH2:8](N)[CH:9]=[CH2:10].[CH2:12]=[CH:13][CH:14]=[CH2:15].[CH3:16]C(C)=O>>[CH3:7][CH:6]1[CH2:15][CH:14]=[CH:13][CH2:12][CH2:8][CH:9]=[CH:10][CH2:2][C:1]([CH3:16])([CH3:3])[N:4]=[CH:5]1

Participants

Reactant 4

HCID 180Acetone

HCID 78451,3-Butadiene

HCID 7853Allylamine

HCID 54364347HCID 54364347, compound

Product 1

HCID 53687623HCID 53687623, compoundYield 80.5%

Procedure

The procedure described in Example 2 is repeated except that 110 g (1.13 mols) of N-isopropylidene-propenylamine [prepared by reacting acetone with allylamine, cf. B. A. Kazanskii et al., Zhurnal Organicheskoi Khimii, Volume 6, No. 11, 2197-9 (1970)] and 108 g (2 mols) of 1,3-butadiene are used. Distillation yields 187.0 g (0.91 mol) of 3,12,12-trimethyl-1-aza-1,5,9-cyclododecatriene; yield 80.5% of theory, based on converted N-isopropylidene-propenylamine (conversion 100%); boiling point 55° C./0.03 mm Hg; nD20 =1.4895.

Workup

customprepared
distillationDistillation

Sources & evidence

ORD record: ord-5e5992742cbb44b9bf19eafbb5571927
Source dataset: uspto-grants-1980_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04213901

Reaction notes

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