Hydrogen Bromide → HCID 54550838, compound

HRID 1906423Notes

Reaction equation

HRID 1906423 reaction equation
C[O:2][C:3]1[CH:4]=[C:5](/[CH:9]=[C:10]2/[CH:11]([N:16]3[CH2:19][CH2:18][CH2:17]3)[CH2:12][CH2:13][CH2:14][CH2:15]/2)[CH:6]=[CH:7][CH:8]=1.Br>O>[OH:2][C:3]1[CH:4]=[C:5]([CH:9]=[C:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH:11]2[N:16]2[CH2:19][CH2:18][CH2:17]2)[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 13504798HCID 13504798, compound

Product 1

HCID 54550838HCID 54550838, compoundYield 76.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
95 °C

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]cyclohexyl]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. temperatureThe resulting mixture was cooled
  2. extractionextracted with diethyl ether
  3. extractionThe ether extract
  4. dry with materialwas dried with magnesium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-e21142f886d7448abf58e950b6609206
Source dataset
uspto-grants-1987_03
Patent number
US04652559

Reaction notes

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