Benzaldehyde → N-benzyl-N-{1-[bis(4-chlorophenyl)methyl]azetidin-3-yl}amine

HRID 277131Notes

Reaction equation

HRID 277131 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([CH:16]([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)[N:17]2[CH2:20][CH:19]([NH2:21])[CH2:18]2)=[CH:12][CH:11]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>ClCCl.C(O)(=O)C>[CH2:1]([NH:21][CH:19]1[CH2:20][N:17]([CH:16]([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)[C:13]2[CH:12]=[CH:11][C:10]([Cl:9])=[CH:15][CH:14]=2)[CH2:18]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 240BenzaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 218965981-[Bis(4-chlorophenyl)methyl]azetidin-3-ylamine

Product 1

HCID 10157628N-benzyl-N-{1-[bis(4-chlorophenyl)methyl]azetidin-3-yl}amine

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

0.134 cm3 of benzaldehyde is added, at room temperature under an argon atmosphere, to a solution of 369 mg of 1-[bis(4-chlorophenyl)methyl]azetidin-3-ylamine in 15 cm3 of dichloromethane. The mixture is cooled to around 0° C., before gradually adding thereto 382 mg of sodium triacetoxyborohydride, and then 70 mm3 of acetic acid. After stirring for 16 hours at room temperature, the mixture is poured over 50 cm3 of a saturated aqueous sodium hydrogen carbonate solution and then extracted with twice 25 cm3 of dichloromethane. The combined organic phases are dried over magnesium sulfate, filtered and concentrated to dryness under reduced pressure (2.7 kPa). The residue obtained is purified by flash chromatography on silica gel [eluent: dichloromethane/methanol (95/5 by volume)]. 0.29 g of N-benzyl-N-{1-[bis(4-chlorophenyl)methyl]azetidin-3-yl}amine is obtained in the form of a colorless oil [1H NMR spectrum (300 MHz, CDCl3, δ ppm):2.71 (broad t, J=7 Hz,:2 H); 3.42 (mt:2 H); 3.49 (mt:1 H); 3.70 (s:2 H); 4.25 (s:1 H); from 7.20 to 7.40 (mt:13 H)].

Workup

  1. additionbefore gradually adding
  2. extractionextracted with twice 25 cm3 of dichloromethane
  3. dry with materialThe combined organic phases are dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  6. customThe residue obtained
  7. customis purified by flash chromatography on silica gel [eluent: dichloromethane/methanol (95/5 by volume)]

Sources & evidence

ORD record
ord-e37c1ea7042b40f3ac8041d5a98b41ea
Source dataset
uspto-grants-2002_03
Patent number
US06355631B1

Reaction notes

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