Maleic Acid → 290334-43-9

HRID 1395907Notes

Reaction equation

HRID 1395907 reaction equation
[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][C:14]([CH:16]([N:18]([CH3:20])[CH3:19])[CH3:17])=[O:15].[C:21]([OH:28])(=[O:27])/[CH:22]=[CH:23]\[C:24]([OH:26])=[O:25]>CO>[C:21]([OH:28])(=[O:27])/[CH:22]=[CH:23]\[C:24]([OH:26])=[O:25].[CH3:19][N:18]([CH3:20])[CH:16]([CH3:17])[C:14]([O:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])=[O:15]

Participants

4

Reactant 2

HCID 444266Maleic AcidHCID 3025823Dodecyl N,N-dimethylalaninate2×

Product 1

HCID 76280826290334-43-9Yield 98.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A stirred solution of DDAIP base 4 (80 g, 280 mmol) in methanol (600 mL) was cooled to 0° C., then maleic acid 16 (32.48 g, 280 mmol) was added in one lot. After addition, the temperature of the reaction mixture was slowly raised to RT and stirred at RT for 12 h; the reaction mixture was monitored by TLC. The reaction mixture was concentrated under vacuum and flushed with ethyl acetate (2×100 mL). The obtained residue was taken in n-hexane (200 mL) and stirred at RT for ½ h (No solid). The reaction mixture was concentrated under vacuum. The obtained sticky solid was kept in deep freezer for 2 h to afford dodecyl 2-(dimethylamino)propanoate maleate salt (17, Nex-20) (111 g, yield: 98.6%) as a solid, mp: 65-70° C. 1H-NMR (400 MHz, CDCl3): δ 0.9 (t, 3H), 1.25 (m, 18H), 1.6 (d, 3H), 1.65 (q, 2H), 2.9 (s, 6H), 4.1 (q, 1H), 4.2 (t, 2H), 6.3 (d, 2H); LCMS: 286 (M++1); HPLC: 80.48%.

Workup

  1. additionAfter addition
  2. concentrationThe reaction mixture was concentrated under vacuum
  3. customflushed with ethyl acetate (2×100 mL)
  4. stirringstirred at RT for ½ h (No solid)
  5. concentrationThe reaction mixture was concentrated under vacuum
  6. waitThe obtained sticky solid was kept in deep freezer for 2 h

Sources & evidence

ORD record
ord-1bcd57ad583f42a58cd4b578179e2296
Source dataset
uspto-grants-2014_12
Patent number
US08900625B2

Reaction notes

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