Azetidine → HCID 54550838, compound

HRID 1719524Notes

Reaction equation

HRID 1719524 reaction equation
[OH:1][C:2]1[CH:3]=[C:4](/[CH:8]=[C:9]2/[CH:10]([N:15]3[CH2:18][CH2:17][CH2:16]3)[CH2:11][CH2:12][CH2:13][CH2:14]/2)[CH:5]=[CH:6][CH:7]=1.N1CCC1>>[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH:10]2[N:15]2[CH2:18][CH2:17][CH2:16]2)[CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 10422AzetidineHCID 13504799HCID 13504799, compound

Product 1

HCID 54550838HCID 54550838, compound

Procedure

A mixture of 1.1 g of (±)-(E)-N-[2[(3-methoxyphenyl)methylene]cyclohexyl]azetidine, prepared by analogy to the preparation of the 4-methoxy compound of Example 5, and 5 ml of 48% hydrogen bromide in water solution was stirred and heated at 95° C. for 2.75 hr. The resulting mixture was cooled and extracted with diethyl ether. The ether extract was dried with magnesium sulfate and evaporated to give 0.8 g of N-[2-[(3-hydroxyphenyl)methylene]cyclohexl]azetidine as an oil which deposited as crystals upon standing overnight. Filtration with diethyl ether gave 0.21 g of this 3-hydroxyphenyl compound as a pale yellow solid. The UV, IR, mass spectrum and NMR analysis indicated the named product was present. Gas chromatography (GC) analysis indicated that this product was a mixture containing about 92% of (±)-(E)-1-[2-[(3-hydroxyphenyl)methylene]cyclohexyl]azetidine, mp 160°-165° C. and 8% of the starting 1-[2-(3-methoxyphenyl)methylene]cyclohexyl]azetidine, mp 136°-137° C.

Workup

  1. filtrationFiltration with diethyl ether
  2. customgave 0.21 g of this 3-hydroxyphenyl compound as a pale yellow solid

Sources & evidence

ORD record
ord-36c5143ff889454291e099fa383390bc
Source dataset
uspto-grants-1985_09
Patent number
US04540690

Reaction notes

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