Isobutylamine → HCID 79269101, compound

HRID 1699129Notes

Reaction equation

HRID 1699129 reaction equation
Br[CH2:2][C:3]([O:5]C(C)(C)C)=[O:4].[CH2:10]([NH2:14])[CH:11]([CH3:13])[CH3:12]>C(OCC)C>[C:11]([N:14]([CH2:10][CH:11]([CH3:13])[CH3:12])[CH2:2][C:3]([OH:5])=[O:4])([CH3:13])([CH3:12])[CH3:10]

Participants

4

Reactant 2

HCID 6558IsobutylamineHCID 79177tert-Butyl bromoacetate

Product 1

HCID 79269101HCID 79269101, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

t-Butyl bromoacetate (8.4 ml, 10.1 g) was added under an atmosphere of argon to a solution of isobutylamine (50 ml, 36.8 g) in diethyl ether (100 ml) at −40° C. with stiming over 5 min. The solution was stirred at this temperature for 1 hr and then at ambient temperature for 18 hr. The mixture was filtered and the filtrate distilled at ambient pressure to remove ether and subsequently excess isobutylamine (b.p. 64-66° C.) and then under reduced pressure to give the product Yield 82% b.p. 68° C./3 mm NMR (CDCl3 300 MHz, ppm) 3.28(2H, s), 2.4(2H, d), 1.72(1H, m), 1.48(9H,s), 0.92(6H,d). m/Z 188.3 (M+H).

Workup

  1. waitat ambient temperature for 18 hr
  2. filtrationThe mixture was filtered
  3. distillationthe filtrate distilled at ambient pressure
  4. customto remove ether and subsequently excess isobutylamine (b.p. 64-66° C.)

Sources & evidence

ORD record
ord-c1712a99c8f24dfd9e0145bca1171321
Source dataset
uspto-grants-2002_02
Patent number
US06344570B1

Reaction notes

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