1-Heptanamine, N-ethyl- → N-heptyl-N-ethyladipamic acid, methyl ester

HRID 36146

Reaction equation

HRID 36146 reaction equation
[CH2:1]([NH:8][CH2:9][CH3:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[CH3:11][O:12][C:13](=[O:21])[CH2:14][CH2:15][CH2:16][CH2:17][C:18](Cl)=[O:19]>C(Cl)Cl>[CH2:1]([N:8]([CH2:9][CH3:10])[C:18](=[O:19])[CH2:17][CH2:16][CH2:15][CH2:14][C:13]([O:12][CH3:11])=[O:21])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

4

Reactant 2

HCID 480381-Heptanamine, N-ethyl-HCID 520737Methyl 6-chloro-6-oxohexanoate

Product 1

HCID 86748668N-heptyl-N-ethyladipamic acid, methyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3.2 gms of the N-heptyl-N-ethylamine in 96 ml of CH2Cl2 are added 5.7 ml of Et3 followed by 3.63 ml of hexanedioic acid monochloride monomethyl ester. This mixture is stirred at room temperature for 18 hours; and after concentrating under vacuum, the residue obtained is partitioned between ethyl acetate and an aqueous 2N HCl solution. The organic layer is separated and washed with aqueous saturated NaHCO3, then brine, and dried over MgSO4. Following filtration and concentration under vacuum, the residue is flash chromatographed on normal phase silica gel using a 3/1 ratio of hexane and ethyl acetate to yield N-heptyl-N-ethyladipamic acid, methyl ester.

Workup

  1. concentrationand after concentrating under vacuum
  2. customthe residue obtained
  3. customis partitioned between ethyl acetate
  4. customThe organic layer is separated
  5. washwashed with aqueous saturated NaHCO3
  6. dry with materialbrine, and dried over MgSO4
  7. filtrationfiltration and concentration under vacuum
  8. customchromatographed on normal phase silica gel using a 3/1 ratio of hexane and ethyl acetate

Sources & evidence

ORD record
ord-52019a04835a4a47853d4fa68da198cb
Source dataset
uspto-grants-1995_05
Patent number
US05412137

Linked notes

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