Hydrochloric Acid → HCID 86739030, compound

HRID 1995648Notes

Reaction equation

HRID 1995648 reaction equation
[ClH:1].[Cl:2][CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1.C(=O)([O-])O.[Na+].[NH2:16][C:17]1[C:22]([C:23]([OH:25])=[O:24])=[C:21]([CH3:26])[C:20]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[C:19]([CH3:32])[CH:18]=1.Cl>C(O)C.O>[ClH:2].[ClH:1].[CH2:30]([O:29][C:27]([C:20]1[C:21]([CH3:26])=[C:22]([C:17]([NH:16][CH2:3][CH2:4][N:5]2[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]2)=[CH:18][C:19]=1[CH3:32])[C:23]([OH:25])=[O:24])=[O:28])[CH3:31]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 74826Piperidine, 1-(2-chloroethyl)-, hydrochlorideHCID 516892Sodium BicarbonateHCID 126858402-Amino-5-ethoxycarbonyl-4,6-dimethylbenzoic acid

Product 1

HCID 86739030HCID 86739030, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

1-(2-Chloroethyl)piperidine hydrochloride (0.85 g) and sodium hydrogen carbonate (1.5 g) were added to a solution of 6-amino-3-ethoxycarbonyl-2,4-dimethylbenzoic acid (1.0 g) in ethanol (10 ml) and water (10 ml). The mixture was stirred at room temperature for 24 hours and then its pH was adjusted to 4-5 by addition of 10% hydrochloric acid. The solution was concentrated under reduced pressure, and the resulting residue was extracted with CHCl3. The CHCl3 extracts were combined, washed with water, and dried over anhydrous MgSO4. The solvent was evaporated, and the residue was recrystallized from ethanol/diethyl ether to give 3-ethoxycarbonyl-2,4-dimethyl-6-(2-piperidinoethylamino)benzoic acid dihydrochloride (1.2 g, 68%). MS: m/e, 348(M+), 304, 303, 259. NMR: δ (ppm CDCl3), 1.37 (3H, t), 1.75 (6H, b), 2.25 (3H, s), 2.41 (3H, s), 3.00 (6H, b), 3.65 (2H, b), 4.36 (2H, q), 6.33 (1H, s), 8.20 (2H, b).

Workup

  1. concentrationThe solution was concentrated under reduced pressure
  2. extractionthe resulting residue was extracted with CHCl3
  3. washwashed with water
  4. dry with materialdried over anhydrous MgSO4
  5. customThe solvent was evaporated
  6. customthe residue was recrystallized from ethanol/diethyl ether

Sources & evidence

ORD record
ord-bff2155bd8d94d9d88783590ce450f5b
Source dataset
uspto-grants-1983_09
Patent number
US04405623

Reaction notes

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