Octanoyl chloride → HCID 43085631, compound

HRID 1075362Notes

Reaction equation

HRID 1075362 reaction equation
[CH2:1]([N:3]([CH2:7][CH3:8])[CH2:4][CH2:5][NH2:6])[CH3:2].C(N(CC)CC)C.[C:16](Cl)(=O)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C(Cl)(Cl)Cl>[CH2:1]([N:3]([CH2:7][CH3:8])[CH2:4][CH2:5][NH:6][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH3:2]

Participants

6

Reactant 4

HCID 8124Octanoyl chlorideHCID 8471TriethylamineHCID 60993N,N-DiethylethylenediamineHCID 21226445Aluminium lithium hydride

Product 1

HCID 43085631HCID 43085631, compoundYield 76.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of N,N-diethylethylenediamine (9.6 g, 0.0826 mol) and 8.4 g (0.0826 mol) of triethylamine in 40 ml of chloroform was added dropwise to the ice cold chloroform solution (40 ml) of octanoyl chloride (13.4 g, 0.0826 mol). After addition, the ice bath was removed and the solution was stirred for 5 hours at room temperature. The reaction mixture was stirred with aqueous sodium bicarbonate for one hour. The organic layer was then dried over magnesium sulfate leaving a yellow liquid which was concentrated in vacuo. The yellow liquid was subject to high vacuum distillation to yield 9.65 g (0.040 mol, 48.3%, b.p.0.05mm =115° C.). The above amide (9.65 g, 0.040 mol) was reduced with lithium aluminum hydride (1.7 g, 0.045 mol) to yield 6.94 g (0.030 mol, 76.1%) of the product after vacuum distillation: (b.p.0.05mm =77° C.). NMR (CDCl3) δ 2.7-2.4 (m, 10H, NCH2 and NHCH2), 1.6 (s, 1H, NH), 1.5 (m, 2H, NHCH2CH2), 1.28 (s, 10H, NHCH2CH2 (CH2)5), 1.01 (t, 6H, NCH2CH3), 0.88 (t, 3H, CH3). Elemental Analysis: Caled. for C14H32N2 (228.41): C, 73.61; H, 14.12; N, 12.26. Found: C, 73.68; H, 14.76; N, 12.12.

Workup

  1. additionAfter addition
  2. customthe ice bath was removed
  3. stirringThe reaction mixture was stirred with aqueous sodium bicarbonate for one hour
  4. dry with materialThe organic layer was then dried over magnesium sulfate leaving a yellow liquid which
  5. concentrationwas concentrated in vacuo
  6. distillationThe yellow liquid was subject to high vacuum distillation
  7. customto yield 9.65 g (0.040 mol, 48.3%, b.p.0.05mm =115° C.)

Sources & evidence

ORD record
ord-6bb988b535ad4ca5af2f39976a19f5b6
Source dataset
uspto-grants-1999_05
Patent number
US05900213

Reaction notes

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