Triethylamine → HCID 58895292, compound

HRID 1676865Notes

Reaction equation

HRID 1676865 reaction equation
[CH3:1][C:2]1([CH2:7][CH2:8][CH:9]=[C:10]([CH3:12])[CH3:11])[CH2:4][CH:3]1[CH2:5][NH2:6].[CH2:13]([O:15][C:16](Cl)=[O:17])[CH3:14].C(N(CC)CC)C>C(OCC)(=O)C>[CH3:1][C:2]1([CH2:7][CH2:8][CH:9]=[C:10]([CH3:12])[CH3:11])[CH2:4][CH:3]1[CH2:5][NH:6][C:16](=[O:17])[O:15][CH2:13][CH3:14]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 23115918HCID 23115918, compound

Product 1

HCID 58895292HCID 58895292, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

1-[2-methyl-2-(4-methylpent-3-en-1-yl)cyclopropyl]methanamine (20.0 g, 0.12 mol) in 150 mL of ethyl acetate and ethylchloroformate (17.9 g, 0.165 mol) were charged to a reaction flask. The reaction mixture was then cooled to 0° C. Triethylamine (23.8 g, 0.165 mol) was slowly added while maintaining the reaction temperature at 0° C. Once the feed was complete the reaction mixture was aged for 2 hours than quenched with saturated sodium chloride solution. Kugelrohr distillation afforded 19.2 g of the product, 67% yield. 1H NMR (500 MHz, CDCl3) S: 0.07-0.12 (m, 1H), 0.44-0.49 (m, 1H), 0.75-0.79 (m, 1H), 1.04-1.06 (2s, 3H), 1.24 (t, J=6.89 Hz, 3H), 1.24-1.42 (m, 1H), 1.29-1.42 (m, 1H), 1.61 (s, 3H), 1.69 (s, 3H), 2.04-2.08 (m, 2H), 2.99-3.35 (m, 2H), 4.11 (q, J=6.82 Hz, 2H), 4.62 (br. s, 1H), 5.07-5.13 (m, 1H).

Workup

  1. temperaturewhile maintaining the reaction temperature at 0° C
  2. customthan quenched with saturated sodium chloride solution
  3. distillationKugelrohr distillation

Sources & evidence

ORD record
ord-e9c95b68f95f41f0be5af63564203f90
Source dataset
uspto-grants-2011_08
Patent number
US08007849B2

Reaction notes

Loading…