Hydrochloric Acid → N-methoxy-N-methylpentanamide

HRID 1958556Notes

Reaction equation

HRID 1958556 reaction equation
[C:1]([OH:7])(=O)[CH2:2][CH2:3][CH2:4][CH3:5].Cl.[CH3:9][NH:10][O:11][CH3:12].CN1CCOCC1.CN(C)CCCN=C=NCC.Cl.C1C=CC2N(O)N=NC=2C=1>ClCCl>[CH3:12][O:11][N:10]([CH3:9])[C:1](=[O:7])[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 79724-MethylmorpholineHCID 7991Pentanoic AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)

Product 1

HCID 3801384N-methoxy-N-methylpentanamideYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Part A: To a magnetically stirred solution of valeric acid (10.9 ml, 0.1 mol) in dichloromethane (200 ml) was successively added: N-methyl-N-methoxy-amine.hydrochloride (10.14 gram, 0.104 mol), N-methylmorpholine (22.9 ml, 0.208 mol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide.HCl (EDCI) (19.92 gram, 0.104 mol) and HOBt (14.04 gram, 0.104 mol) and the resulting mixture was reacted for 20 hours at room temperature. The obtained suspension was successively washed with water, aqueous citric acid (a solution of 24 gram citric acid in 250 ml H2O) and 5% aqueous NaHCO3. The organic layer was dried over Na2SO4, filtered and concentrated to give pentanoic acid methoxy-methyl-amide (12.31 gram, 85% yield) as a colorless oil. 1H-NMR (400 MHz, CDCl3) δ 0.93 (t, J=7, 3H), 1.31-1.43 (m, 2H), 1.57-1.66 (m, 2H), 2.42 (br t, J=7, 2H), 3.18 (s, 3H), 3.69 (s, 3H).

Workup

  1. washThe obtained suspension was successively washed with water, aqueous citric acid (a solution of 24 gram citric acid in 250 ml H2O) and 5% aqueous NaHCO3
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-e0278f4c53f14c3088c1d1c8ad4c18c9
Source dataset
uspto-grants-2013_04
Patent number
US08410135B2

Reaction notes

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