N-Methylbutylamine → HCID 19933896, compound

HRID 1533975Notes

Reaction equation

HRID 1533975 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11](Cl)=[O:12].[CH3:14][NH:15][CH2:16][CH2:17][CH2:18][CH3:19].C(N(C(C)C)CC)(C)C>ClCCl>[CH2:16]([N:15]([CH3:14])[C:11]([C:2]1[CH:3]=[CH:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:1]=1)=[O:12])[CH2:17][CH2:18][CH3:19]

Participants

5

Reactant 3

HCID 8068N-MethylbutylamineHCID 752462-Naphthoyl chlorideHCID 81531Diisopropylethylamine

Product 1

HCID 19933896HCID 19933896, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2-Naphthoyl chloride (3.81 g 0.020 moles) dissolved in dichloromethane (10 ml) was added dropwise to an ice cold solution of N-methylbutylamine (1.74 g, 0.020 moles) and diisopropylethylamine (4.5 ml, 0.025 moles) in dichloromethane (40 ml). The mixture was stirred at room temperature for 18 hours and evaporated in vacuo. The residue was taken up into dichloromethane (50 ml), washed with 2M HCl (2×25 ml), dried (MgSO4) then evaporated in vacuo to give N-butyl-N-methyl-naphthalene-2-carboxamide (4.6 g, 0.019 moles) as a yellow oil.

Workup

  1. customevaporated in vacuo
  2. washwashed with 2M HCl (2×25 ml)
  3. dry with materialdried (MgSO4)
  4. customthen evaporated in vacuo

Sources & evidence

ORD record
ord-6856ffb4885347769c2c85aa7ae54c79
Source dataset
uspto-grants-1992_02
Patent number
US05086073

Reaction notes

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