Hydrochloride methanol → HCID 67315093, compound

HRID 1012572Notes

Reaction equation

HRID 1012572 reaction equation
[CH2:1]([N:4]([CH2:19][CH2:20][CH3:21])[CH2:5][CH2:6][CH2:7][CH2:8][NH:9][CH2:10][C:11]1[CH:18]=[CH:17][C:14]([CH2:15][NH2:16])=[CH:13][CH:12]=1)[CH2:2][CH3:3].[ClH:22].CO>CO>[ClH:22].[CH2:19]([N:4]([CH2:1][CH2:2][CH3:3])[CH2:5][CH2:6][CH2:7][CH2:8][NH:9][CH2:10][C:11]1[CH:12]=[CH:13][C:14]([CH2:15][NH2:16])=[CH:17][CH:18]=1)[CH2:20][CH3:21]

Participants

4

Reactant 2

HCID 21893726Hydrochloride methanolHCID 59850548HCID 59850548, compound

Product 1

HCID 67315093HCID 67315093, compoundYield 74.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

7.2 g of unpurified 4-[(4-dipropylaminobutyl)amino]methylbenzylamine (5a) synthesized in Example 12 was diluted with 20 ml of methanol. 32.9 g (3.6 equivalents) of a 10% hydrochloric acid-methanol solution was added dropwise to the mixture under cooling with ice. The mixture was stirred for one hour at a same temperature, and then concentrated. Hexane was added to the residue obtained, and the resulting mixture was azeotropically distillated. This operation was repeated three times to completely remove methanol, thereby obtaining white crystals. The crystals were dissolved in 120 ml of a mixed solvent (IPA:MeOH=3:1) at 70° C. The solution was stirred overnight at room temperature to precipitate white crystals. The crystals were filtered and dried under reduced pressure, thereby obtaining 7.81 g of 4-[(4-dipropylaminobutyl)amino]methylbenzylamine hydrochloride (5aa) (yield: 74.9%). m. p. 205 to 210° C.

Workup

  1. temperatureunder cooling with ice
  2. concentrationconcentrated
  3. additionHexane was added to the residue
  4. customobtained
  5. customobtaining white crystals
  6. stirringThe solution was stirred overnight at room temperature
  7. customto precipitate white crystals
  8. filtrationThe crystals were filtered
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-a73df183efd8448eb83f2ab0799caf7b
Source dataset
uspto-grants-2011_07
Patent number
US07977512B2

Reaction notes

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