Methylamine → HCID 15053459, compound

HRID 2081466Notes

Reaction equation

HRID 2081466 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][CH:15]=1)[O:5][CH:6]1[CH2:9][N:8]([C:10](Cl)=[O:11])[CH2:7]1.[CH3:16][NH2:17]>O1CCCC1.O>[CH3:16][NH:17][C:10]([N:8]1[CH2:9][CH:6]([O:5][C:4]2[CH:13]=[CH:14][CH:15]=[C:2]([CH3:1])[CH:3]=2)[CH2:7]1)=[O:11]

Participants

5

Reactant 2

HCID 6329MethylamineHCID 19799586HCID 19799586, compound

Product 1

HCID 15053459HCID 15053459, compoundYield 18.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

A stirred solution of 3.92 g (0.01 mole) of 3-(3-methylphenoxy)-1-azetidinecarbonyl chloride in 15 ml of tetrahydrofuran was treated with 2.4 g (0.03 mole) of 40% aqueous monomethylamine and stirring continued for 17 hr. The reaction mixture was diluted with 200 ml of water. The reddish oil residue was cooled to -78° C. whereupon it crystallized (4.28 g). Recrystallization from benzene-ligroin gave 400 mg of fine white crystals, m.p. 143°-144° C. Addition of more ligroin yielded an additional 800 mg of "cream" colored crystalline product, m.p. 138°-142° C. The two fractions were combined and recrystallized from ethanol-isopropyl ether, yielding 600 mg (27.3%) of fine white crystals, m.p. 143°-144° C.

Workup

  1. customcrystallized (4.28 g)
  2. customRecrystallization from benzene-ligroin

Sources & evidence

ORD record
ord-b0ab3cd40c3e4333a49b3b78916d4c82
Source dataset
uspto-grants-1993_02
Patent number
US05183902

Reaction notes

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