Acetic Acid → (4-{[(4-dipropylamino-butyl)-methyl-amino]-methyl}-benzyl)-carbamic Acid t-butyl Ester

HRID 348719Notes

Reaction equation

HRID 348719 reaction equation
[C:1]([O:5][C:6](=[O:28])[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][NH:16][CH2:17][CH2:18][CH2:19][CH2:20][N:21]([CH2:25][CH2:26][CH3:27])[CH2:22][CH2:23][CH3:24])=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].C=O.[C:31]([BH3-])#N.[Na+].C(O)(=O)C>CO>[C:1]([O:5][C:6](=[O:28])[NH:7][CH2:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][N:16]([CH2:17][CH2:18][CH2:19][CH2:20][N:21]([CH2:22][CH2:23][CH3:24])[CH2:25][CH2:26][CH3:27])[CH3:31])=[CH:13][CH:14]=1)([CH3:3])([CH3:4])[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 66941782{4-[(4-dipropylamino-butylamino)-methyl]-benzyl}-carbamic Acid t-butyl Ester

Product 1

HCID 66941863(4-{[(4-dipropylamino-butyl)-methyl-amino]-methyl}-benzyl)-carbamic Acid t-butyl EsterYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The compound (625.7 mg) obtained in Example 115-1 was dissolved in methanol (25.0 ml) and added with a 36% formaldehyde aqueous solution (0.246 ml) and sodium cyanoborohydride (220.9 mg). The solution was adjusted to pH 5 with acetic acid and stirred at room temperature for 27 hours. The reaction solution was concentrated under reduced pressure and the residue was added with a 1 mol/l sodium hydroxide aqueous solution, followed by separation/extraction with chloroform. After having been washed with saturated saline solution, the extract was dried with anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified through silica gel column chromatography (chloroform/ethyl acetate), thereby obtaining the subject compound (648.1 mg) as a colorless oily substance.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. additionthe residue was added with a 1 mol/l sodium hydroxide aqueous solution
  3. extractionfollowed by separation/extraction with chloroform
  4. washAfter having been washed with saturated saline solution
  5. dry with materialthe extract was dried with anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified through silica gel column chromatography (chloroform/ethyl acetate)

Sources & evidence

ORD record
ord-715f639f01254de3bf8d893c9156d6b1
Source dataset
uspto-grants-2007_02
Patent number
US07176227B2

Reaction notes

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