Hydrogen Bromide → HCID 10243700, compound

HRID 364142Notes

Reaction equation

HRID 364142 reaction equation
Br.Cl.C[O:4][C:5]1[CH:6]=[CH:7][C:8]2[O:21][CH2:20][C@H:12]3[N:13]([CH2:17][CH2:18][CH3:19])[CH2:14][CH2:15][CH2:16][C@@H:11]3[C:9]=2[CH:10]=1>>[OH:4][C:5]1[CH:6]=[CH:7][C:8]2[O:21][CH2:20][C@H:12]3[N:13]([CH2:17][CH2:18][CH3:19])[CH2:14][CH2:15][CH2:16][C@@H:11]3[C:9]=2[CH:10]=1

Participants

3

Reactant 2

HCID 260Hydrogen BromideHCID 14151579HCID 14151579, compound

Product 1

HCID 10243700HCID 10243700, compound

Procedure

A mixture of 21.6 l of 47-49% hydrobromic acid and 2.27 kg of trans-9-methoxy-4-propyl-1,2,3,4a,5,10b-hexahydro-4H-[1]-benzopyrano[3,4-b]pyridine hydrochloride is stirred and heated at 105°-110° for 2 hours. Most of the hydrobromic acid is then removed by distillation (125°/3 mmHg), a solution of 10.5 l of methanol and 9.5 l of water is added and the suspension heated to 75°. The hot mixture is cautiously treated with 2.2 l of 4N sodium hydroxide solution to pH 8, cooled to 10° and filtered. The collected solids are washed five times with 1 l of water each and dried (68°/3 mmHg) to yield trans-9-hydroxy-4-propyl-1,2,3,4a,5,10b-hexahydro-4H-[1]-benzopyrano[3,4-b]pyridine, m.p. 194°-196°.

Workup

  1. temperatureheated at 105°-110° for 2 hours
  2. customMost of the hydrobromic acid is then removed by distillation (125°/3 mmHg)
  3. additiona solution of 10.5 l of methanol and 9.5 l of water is added
  4. temperaturethe suspension heated to 75°
  5. additionThe hot mixture is cautiously treated with 2.2 l of 4N sodium hydroxide solution to pH 8
  6. temperaturecooled to 10°
  7. filtrationfiltered
  8. washThe collected solids are washed five times with 1 l of water each and
  9. customdried (68°/3 mmHg)

Sources & evidence

ORD record
ord-d73f78a6fa8946e4835ae45ae7b9f331
Source dataset
uspto-grants-1986_08
Patent number
US04604397

Reaction notes

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