Hydrogen Bromide → 5-[(Piperidin-1-yl)methyl]-5,6,7,8-tetrahydronaphthalen-1-ol

HRID 1905748Notes

Reaction equation

HRID 1905748 reaction equation
C[O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][CH2:7][CH:8]2[CH2:13][N:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.Br>C(O)(=O)C>[OH:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][CH2:7][CH:8]2[CH2:13][N:14]1[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 13756027HCID 13756027, compound

Product 1

HCID 137111145-[(Piperidin-1-yl)methyl]-5,6,7,8-tetrahydronaphthalen-1-ol

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of the 5-methoxy compound from step 4 above (41 g), 47-49% hydrobromic acid (410 ml) in glacial acetic acid (410 ml) is stirred at reflux under nitrogen for 2.5 hours. The cooled reaction mixture is poured into ice/water, made alkaline and the pH adjusted until no more cloudiness appears. The resulting oil is extracted into ether, washed, dried, filtered and the filtrate evaporated in vacuo forming a solid residue which is recrystallized from hot acetonitrile yielding the desired product as a crystalline solid, M.P.=129°-131° C.

Workup

  1. temperatureat reflux under nitrogen for 2.5 hours
  2. customThe cooled reaction mixture
  3. extractionThe resulting oil is extracted into ether
  4. washwashed
  5. customdried
  6. filtrationfiltered
  7. customthe filtrate evaporated in vacuo
  8. customforming a solid residue which
  9. customis recrystallized from hot acetonitrile yielding the desired product as a crystalline solid, M.P.=129°-131° C.

Sources & evidence

ORD record
ord-b636924e5c204c3b9ce7f1ce3eb560f0
Source dataset
uspto-grants-1987_03
Patent number
US04647559

Reaction notes

Loading…