Water → (1-Benzhydryl-azetidin-3-yl)-(2-methoxy-phenyl)-methyl-amine

HRID 1066906Notes

Reaction equation

HRID 1066906 reaction equation
[CH3:1][NH:2][C:3]1[C:4](=[CH:7][CH:8]=[CH:9][CH:10]=1)[O:5][CH3:6].C([O-])([O-])=O.[K+].[K+].[C:17]1([CH:23]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[N:24]2[CH2:27][CH:26](S(C)(=O)=O)[CH2:25]2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.O>C(#N)C>[CH:23]([N:24]1[CH2:27][CH:26]([N:2]([C:3]2[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=2[O:5][CH3:6])[CH3:1])[CH2:25]1)([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 27595792-Methoxy-N-methylanilineHCID 155219691-Benzhydryl-3-(methylsulfonyl)azetidine

Product 1

HCID 21196806(1-Benzhydryl-azetidin-3-yl)-(2-methoxy-phenyl)-methyl-amineYield 25.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 0.65 g of N-methyl o-anisidine in 15 mL of acetonitrile, was added 0.280 g of K2CO3, followed by 0.650 g of 1-(diphenylmethyl)-3-methane sulfonyl azetidine. The reaction mixture was heated at 80° C. for 1 h then at 50° C. overnight. Water was added and the mixture was extracted with ether. The organic phase was dried and the solvent was removed under vacuo. The product was filtered through 100 mL of silica gel, eluting a with 15% ethyl acetate/hexanes then 25% ethyl acetate/hexanes to give 0.200 g of the desired product: mp 91-95° C. MS (ES) m/z (relative intensity): 356 (M++H).

Workup

  1. customat 50° C.
  2. customovernight
  3. extractionthe mixture was extracted with ether
  4. customThe organic phase was dried
  5. customthe solvent was removed under vacuo
  6. filtrationThe product was filtered through 100 mL of silica gel
  7. washeluting a with 15% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-5e6e155447f34d639c8d0f88bb7dc6a9
Source dataset
uspto-grants-2001_06
Patent number
US06245799B1

Reaction notes

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