Benzylamine → 6-heptynoic acid N-benzylamide

HRID 1823894Notes

Reaction equation

HRID 1823894 reaction equation
CN(C)CCCN=C=NCC.[C:12]([OH:20])(=O)[CH2:13][CH2:14][CH2:15][CH2:16][C:17]#[CH:18].[CH2:21]([NH2:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C>O1CCCC1.C(=O)([O-])O.[Na+]>[CH2:21]([NH:28][C:12](=[O:20])[CH2:13][CH2:14][CH2:15][CH2:16][C:17]#[CH:18])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

8

Reactant 5

HCID 7504BenzylamineHCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 43779506-Heptynoic acid

Product 1

HCID 597122936-heptynoic acid N-benzylamideYield 112.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Procedure

1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (3.3 g, 17.4 mmol) was added to a mixture of 6-heptynoic acid (1.1 g, 8.7 mmol), benzylamine (950 μl, 8.7 mmol), 1-hydroxybenzotriazole (1.2 g, 8.7 mmol) and triethylamine (2.4 ml, 17.4 mmol) in tetrahydrofuran (25 ml) and the mixture was stirred at room temperature for 16 hours. The reaction was diluted with sodium hydrogen carbonate (sat, 60 ml) and extracted with ethyl acetate (2×100 ml). The extracts were washed with brine, dried (MgSO4) and evaporated in vacuo to provide 6-heptynoic acid N-benzylamide as a brown solid (2.1 g, 99%). (ES+) 216 ([MH]+).

Workup

  1. extractionextracted with ethyl acetate (2×100 ml)
  2. washThe extracts were washed with brine
  3. dry with materialdried (MgSO4)
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-3f25a3e1b4ba4e40a1efd00c86651153
Source dataset
uspto-grants-2006_05
Patent number
US07041688B2

Reaction notes

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