HCID 53847304, compound → HCID 22795184, compound

HRID 1973684Notes

Reaction equation

HRID 1973684 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([C@H:9]2[CH2:14][CH2:13][CH2:12][CH2:11][C@H:10]2[N:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)[CH:6]=[CH:7][CH:8]=1>Br.O>[OH:2][C:3]1[CH:4]=[C:5]([C@H:9]2[CH2:14][CH2:13][CH2:12][CH2:11][C@H:10]2[N:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 1

HCID 53847304HCID 53847304, compound

Product 1

HCID 22795184HCID 22795184, compound

Reagents, catalysts & solvents 2

HCID 260Hydrogen BromideSolventHCID 962WaterSolvent

Procedure

(1) The above oil (19g) was boiled in 47% hydrobromic acid (60 ml) for six hours. The cooled solution was diluted with water, washed with ether, basified and ether extracted. The dried extract was evaporated. The residue was triturated with petroleum ether (b.p. 40° to 60° C) and crystallised from petroleum ether (b.p. 60° to 80° C)/ ethyl acetate to give cis-2-(3-hydroxyphenyl)-1-pyrrolidinocyclohexane (12g), m.p. 124° to 126° C.

Workup

  1. washwashed with ether
  2. extractionether extracted
  3. extractionThe dried extract
  4. customwas evaporated
  5. customThe residue was triturated with petroleum ether (b.p. 40° to 60° C)
  6. customcrystallised from petroleum ether (b.p. 60° to 80° C)/ ethyl acetate

Sources & evidence

ORD record
ord-239a5fa649b640afa3a2d6d118becc84
Source dataset
uspto-grants-1976_12
Patent number
US03998843

Reaction notes

Loading…