Dichloromethane → N-(2-diethylaminoethoxy-2-oxoethyl)-N-[3,5-bis(decyloxy)phenyl]glycine monohydrochloride salt

HRID 1110234Notes

Reaction equation

HRID 1110234 reaction equation
[CH2:1]([O:11][C:12]1[CH:13]=[C:14]([N:29]2[CH2:34][C:33](=[O:35])[O:32][C:31](=[O:36])[CH2:30]2)[CH:15]=[C:16]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH:17]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[CH2:37]([N:39]([CH2:43][CH3:44])[CH2:40][CH2:41][OH:42])[CH3:38].C(Cl)[Cl:46]>>[ClH:46].[CH2:37]([N:39]([CH2:43][CH3:44])[CH2:40][CH2:41][O:42][C:33](=[O:35])[CH2:34][N:29]([C:14]1[CH:15]=[C:16]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH:17]=[C:12]([O:11][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])[CH:13]=1)[CH2:30][C:31]([OH:36])=[O:32])[CH3:38]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 7497DiethylethanolamineHCID 193890794-[3,5-Bis(decyloxy)phenyl]2,6-morpholinedione

Product 1

HCID 21808303N-(2-diethylaminoethoxy-2-oxoethyl)-N-[3,5-bis(decyloxy)phenyl]glycine monohydrochloride saltYield 82%

Procedure

A solution of 0.43 g (0.85 mmol) of 4-[3,5-bis(decyloxy)phenyl]2,6-morpholinedione and 0.23 ml (1.71 mmol) of N,N-diethylethanolamine in 40 ml of methylene chloride was kept at room temperature for 3.5 days. The solvent was removed at reduced pressure and the residue was dissolved in ethyl acetate. The extract was washed with water and then with 0.5N HCl, dried and concentrated at reduced pressure to a yellow foam which was dissolved in ether and cooled. Filtration gave 0.46 g (82% yield, mp 89°-91°) of N-(2-diethylaminoethoxy-2-oxoethyl)-N-[3,5-bis(decyloxy)phenyl]glycine monohydrochloride salt.

Workup

  1. customThe solvent was removed at reduced pressure
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washThe extract was washed with water
  4. dry with materialwith 0.5N HCl, dried
  5. concentrationconcentrated at reduced pressure to a yellow foam which
  6. dissolutionwas dissolved in ether
  7. temperaturecooled
  8. filtrationFiltration

Sources & evidence

ORD record
ord-783fcb93613a4787b0ddd33cfa3e5717
Source dataset
uspto-grants-1994_06
Patent number
US05324747

Reaction notes

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