1-Methylpyrrolidine-2-methylamine → N-(1-methyl-2-pyrrolidylmethyl)-1,4-benzodioxane-5-carboxamide

HRID 1659998

Reaction equation

HRID 1659998 reaction equation
CO[C:3]([C:5]1[C:14]2[O:13][CH2:12][CH2:11][O:10][C:9]=2[CH:8]=[C:7](S(=O)(=O)NC)[CH:6]=1)=[O:4].[CH3:20][N:21]1[CH2:25][CH2:24][CH2:23][CH:22]1[CH2:26][NH2:27]>C(O)(=O)C.O>[CH3:20][N:21]1[CH2:25][CH2:24][CH2:23][CH:22]1[CH2:26][NH:27][C:3]([C:5]1[C:14]2[O:13][CH2:12][CH2:11][O:10][C:9]=2[CH:8]=[CH:7][CH:6]=1)=[O:4]

Participants

5

Reactant 2

HCID 1173001-Methylpyrrolidine-2-methylamineHCID 54343297Methyl-7-methylsulfamoyl-1,4-benzodioxane-5-carboxylate

Product 1

HCID 53775438N-(1-methyl-2-pyrrolidylmethyl)-1,4-benzodioxane-5-carboxamideYield 112%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Procedure

169 g of methyl-7-methylsulfamoyl-1,4-benzodioxane-5-carboxylate, 53 ml of water and 81 g of 1-methyl-2-aminomethylpyrrolidine were introduced into a balloon flask provided with a reflux condenser. The mixture was heated on a water bath until a test sample was totally soluble in dilute acids. The resulting crystals were dissolved in a solution of 50 ml of acetic acid in 1,250 ml of water and then the solution was filtered over carbon black and the base was reprecipitated by the addition of 100 ml of 20% ammonia. The crystals were dried off, washed with water and dried. 182 g of N-(1-methyl-2-pyrrolidylmethyl)-1,4-benzodioxane-5-carboxamide was produced (M.P.: 189°-190° C.; yield: 83.6%).

Workup

  1. customprovided with a reflux condenser
  2. temperatureThe mixture was heated on a water bath until a test sample
  3. filtrationthe solution was filtered over carbon black
  4. customthe base was reprecipitated by the addition of 100 ml of 20% ammonia
  5. customThe crystals were dried off
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-bbff3781b6b24961a32cfb03d29ef7d9
Source dataset
uspto-grants-1981_12
Patent number
US04306072

Linked notes

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