Triethylamine → 1-Benzhydryl-N-methylazetidine-3-carboxamide

HRID 492916Notes

Reaction equation

HRID 492916 reaction equation
[CH:1]([N:14]1[CH2:17][CH:16]([C:18]([OH:20])=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.[CH2:21]([N:23](CC)CC)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.Cl.CN>CN(C)C=O>[CH3:21][NH:23][C:18]([CH:16]1[CH2:17][N:14]([CH:1]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:15]1)=[O:20]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 27354401-(Diphenylmethyl)azetidine-3-carboxylic acidHCID 6364545Methylamine hydrochloride

Product 1

HCID 137728491-Benzhydryl-N-methylazetidine-3-carboxamideYield 74.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-benzhydrylazetidin-3-carboxylic acid (654 mg) in N,N-dimethylformamide (4.0 ml) were added triethylamine (1.0 ml), benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (1.63 g) and methylamine hydrochloride (248 mg), followed by stirring at room temperature for 61.5 hours. The reaction mixture was partitioned between ethyl acetate and water. The organic layer was washed with brine, and dried over anhydrous sodium sulfate. The organic layer was concentrated to give a residue, which was purified by silica gel column chromatography (eluent; ethyl acetate). Fractions containing the target compound were concentrated to provide the titled compound (509 mg, 74.1%) as yellow crystals.

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationThe organic layer was concentrated
  5. customto give a residue, which
  6. customwas purified by silica gel column chromatography (eluent; ethyl acetate)
  7. additionFractions containing the target compound
  8. concentrationwere concentrated

Sources & evidence

ORD record
ord-4d1f8cbffce44eb39e7d2ebbeadc5db5
Source dataset
uspto-grants-2009_05
Patent number
US07531532B2

Reaction notes

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