Sodium Bicarbonate → N-[4-[(N-methyl-N-(tetrahydropyran-4-yl)aminomethyl)]phenyl]-N-[7-(4-methylphenyl)-2,3-dihydro-1-benzooxepin-4-yl]methylamine

HRID 1169378Notes

Reaction equation

HRID 1169378 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]3[O:17][CH2:16][CH2:15][C:14]([CH:18]=O)=[CH:13][C:12]=3[CH:20]=2)=[CH:4][CH:3]=1.[CH3:21][N:22]([CH2:29][C:30]1[CH:36]=[CH:35][C:33]([NH2:34])=[CH:32][CH:31]=1)[CH:23]1[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>ClCCCl>[CH3:21][N:22]([CH2:29][C:30]1[CH:31]=[CH:32][C:33]([NH:34][CH2:18][C:14]2[CH2:15][CH2:16][O:17][C:11]3[CH:10]=[CH:9][C:8]([C:5]4[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][CH:6]=4)=[CH:20][C:12]=3[CH:13]=2)=[CH:35][CH:36]=1)[CH:23]1[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1

Participants

6

Reactant 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydride2×HCID 9877845(4-Amino-benzyl)-methyl-(tetrahydro-pyran-4-yl)-amineHCID 229901807-(4-Methylphenyl)-2,3-dihydro-1-benzooxepine-4-carbaldehyde

Product 1

HCID 70024138N-[4-[(N-methyl-N-(tetrahydropyran-4-yl)aminomethyl)]phenyl]-N-[7-(4-methylphenyl)-2,3-dihydro-1-benzooxepin-4-yl]methylamineYield 26%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Into a solution of 7-(4-methylphenyl)-2,3-dihydro-1-benzooxepine-4-carbaldehyde (191 mg)) and 4-[N-methyl-N-(tetrahydropyran-4-yl)aminomethyl]aniline (159 mg) in 1,2-dichloroethane (5 ml) was added sodium triacetoxyborohydride (168 mg). The resulting mixture was stirred at room temperature for 4.5 hours, additional sodium triacetoxyborohydride (76 mg) was added thereto and the resulting mixture was stirred further for 4 days. The reaction mixture was mixed with an aqueous solution of sodium bicarbonate under ice cooling and was extracted with dichloromethane, and the extract was washed with an aqueous solution of sodium chloride. The extract was dried (anhydrous magnesium sulfate) and was then concentrated under reduced pressure. The residue was subjected to purification using silica gel column chromatography (ethyl acetate/methanol=10/1), 4 N hydrochloric acid was added to the resulting product and the precipitate was collected by filtration and was washed with ethyl acetate to obtain N-[4-[(N-methyl-N-(tetrahydropyran-4-yl)aminomethyl)]phenyl]-N-[7-(4-methylphenyl)-2,3-dihydro-1-benzooxepin-4-yl]methylamine (compound 34) (88 mg) as a light yellow powder.

Workup

  1. stirringthe resulting mixture was stirred further for 4 days
  2. extractionwas extracted with dichloromethane
  3. washthe extract was washed with an aqueous solution of sodium chloride
  4. dry with materialThe extract was dried (anhydrous magnesium sulfate)
  5. concentrationwas then concentrated under reduced pressure
  6. customThe residue was subjected to purification
  7. additionwas added to the resulting product
  8. filtrationthe precipitate was collected by filtration
  9. washwas washed with ethyl acetate

Sources & evidence

ORD record
ord-10088bd2952d405da2878d45d1da96dd
Source dataset
uspto-grants-2003_09
Patent number
US06627651B1

Reaction notes

Loading…