Sodium Bicarbonate → HCID 178497372, compound

HRID 18620Notes

Reaction equation

HRID 18620 reaction equation
Cl.Cl.[CH:3]1([N:6]2[CH2:11][CH2:10][CH:9]([NH2:12])[CH2:8][CH2:7]2)[CH2:5][CH2:4]1.C([O-])(O)=[O:14].[Na+].[CH3:18][O:19][C:20]([C:22]1[CH:34]=[CH:33][C:25]2[NH:26][C:27]([C:29](Cl)(Cl)Cl)=[N:28][C:24]=2[CH:23]=1)=[O:21]>C1COCC1.O>[CH3:18][O:19][C:20]([C:22]1[CH:34]=[CH:33][C:25]2[NH:26][C:27]([C:29](=[O:14])[NH:12][CH:9]3[CH2:10][CH2:11][N:6]([CH:3]4[CH2:5][CH2:4]4)[CH2:7][CH2:8]3)=[N:28][C:24]=2[CH:23]=1)=[O:21]

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 467352434-Amino-1-cyclopropylpiperidine dihydrochlorideHCID 178497356HCID 178497356, compound

Product 1

HCID 178497372HCID 178497372, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of 7.53 g (35.3 mmol) 1-cyclopropyl-piperidin-4-ylamine dihydrochloride and 32.39 g (0.386 mol) NaHCO3 in 1300 mL THF and 370 mL water a solution of 11.79 g (32.1 mmol) 2-trichloromethyl-1H-benzoimidazole-5-carboxylic acid methyl ester in 360 mL THF was added. The reaction mixture was stirred vigorously for 2 h at RT. The THF was evaporated. The precipitate was filtered off and treated twice with about 300 mL of a saturated NaHCO3-solution under ultrasonic conditions. After filtration the resulting solid was washed twice with 150 mL water and dried under reduced pressure at 45° C. to give pure 2-(1-cyclopropyl-piperidin-4-ylcarbamoyl)-1H-benzoimidazole-5-carboxylic methyl ester in form of a light brown crystalline material.

Workup

  1. additionwas added
  2. customThe THF was evaporated
  3. filtrationThe precipitate was filtered off
  4. additiontreated twice with about 300 mL of a saturated NaHCO3-solution under ultrasonic conditions
  5. filtrationAfter filtration the resulting solid
  6. washwas washed twice with 150 mL water
  7. customdried under reduced pressure at 45° C.

Sources & evidence

ORD record
ord-7673bfbca3c9446ca94ccb3fb7b2596e
Source dataset
uspto-grants-2010_06
Patent number
US07741341B2

Reaction notes

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