Allyl isocyanate → 3-[2-(trifluoromethyl)-4'-chlorobenzhydryloxy]-N-(allyl)azetidine-1-carboxamide

HRID 1785712Notes

Reaction equation

HRID 1785712 reaction equation
Cl.[F:2][C:3]([F:24])([F:23])[C:4]1[CH:22]=[CH:21][CH:20]=[CH:19][C:5]=1[CH:6]([O:14][CH:15]1[CH2:18][NH:17][CH2:16]1)[C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=1.C(=O)([O-])[O-].[CH2:29]([N:32]=[C:33]=[O:34])[CH:30]=[CH2:31]>C(Cl)Cl>[F:24][C:3]([F:2])([F:23])[C:4]1[CH:22]=[CH:21][CH:20]=[CH:19][C:5]=1[CH:6]([O:14][CH:15]1[CH2:18][N:17]([C:33]([NH:32][CH2:29][CH:30]=[CH2:31])=[O:34])[CH2:16]1)[C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 15123Allyl isocyanateHCID 19660Carbonate IonHCID 689024633-[2-(Trifluoromethyl)-4'-chlorobenzhydryloxy]azetidine hydrochloride

Product 1

HCID 112817143-[2-(trifluoromethyl)-4'-chlorobenzhydryloxy]-N-(allyl)azetidine-1-carboxamideYield 61%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3-[2-(trifluoromethyl)-4′-chlorobenzhydryloxy]azetidine hydrochloride (98) (100 mg, 0.28 mmol) in anhydrous DCM (3 mL) was added MP-carbonate (3.01 mmol/g; 275 mg, 0.84 mmol) and allyl isocyanate (25 μL, 0.28 mmol). The resultant mixture was shaken at ambient temperature for 16 h, after which time it was poured onto a DCM-wetted SCX-2 (1 g) cartridge. The sample was eluted with DCM (18 mL), then evaporated to afford the desired product (72 mg, 61%).

Workup

  1. washThe sample was eluted with DCM (18 mL)
  2. customevaporated

Sources & evidence

ORD record
ord-fbbe158230a44abcad8b7d125cde9f22
Source dataset
uspto-grants-2009_03
Patent number
US07504522B2

Reaction notes

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