Benzylamine → HCID 18767767, compound

HRID 2300214Notes

Reaction equation

HRID 2300214 reaction equation
[CH:1]([N:14]1[CH2:17][CH:16](OS(C)(=O)=O)[CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:23]([NH2:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CN1C(=O)N(C)CCC1.CCOCC>[CH:1]([N:14]1[CH2:17][CH:16]([NH:30][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 7504BenzylamineHCID 27587161-(Diphenylmethyl)azetidin-3-yl methanesulfonate

Product 1

HCID 18767767HCID 18767767, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-Solvent

Conditions

Temperature
70 °C

Procedure

To a solution of methanesulfonic acid 1-benzhydrylazetidin-3-yl ester (0.32 g, 1 mmol) in N,N′-dimethylpropyleneurea (0.5 ml) was added benzylamine (0.5 ml, 5 mmol), and the mixture was stirred at 70° C. for 18 h. It was then cooled to room temperature and diluted with ether (30 ml). The resulting suspension was filtered and the ether solution was evaporated. The residue was partitioned between hexanes and water, and hexanes solution was washed with saturated sodium bicarbonate solution and dried over anhydrous sodium sulfate. It was then filtered through a pad of silica gel, and the filter pad was eluted with a 1:1 mixture of ether-hexanes. Evaporation of solvents followed by trituration with isooctane gave 0.22 g of a white solid; m.p. 73-75° C.; MS (ES) m/z 329.0 (MH+); HRMS (El) Calcd. for C23H24N2 (M+): 328.1940, Found: 328.1936.

Workup

  1. temperatureIt was then cooled to room temperature
  2. filtrationThe resulting suspension was filtered
  3. customthe ether solution was evaporated
  4. customThe residue was partitioned between hexanes and water, and hexanes solution
  5. washwas washed with saturated sodium bicarbonate solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationIt was then filtered through a pad of silica gel
  8. washthe filter pad was eluted with a 1:1 mixture of ether-hexanes
  9. customEvaporation of solvents

Sources & evidence

ORD record
ord-4c80959a68bc4e31be6d07bebb780312
Source dataset
uspto-grants-2002_12
Patent number
US06498170B2

Reaction notes

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