Hydrochloric Acid → HCID 70113588, compound

HRID 429409Notes

Reaction equation

HRID 429409 reaction equation
C[O:2][C:3]1[CH:12]=[C:11]2[C:6]([C@H:7]([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][N:28]4[CH2:32][CH2:31][CH2:30][CH2:29]4)=[CH:21][CH:20]=3)[C@H:8]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:9][O:10]2)=[CH:5][CH:4]=1.N1C=CC=CC=1.[ClH:39].O>[Cl-].[NH+]1C=CC=CC=1>[ClH:39].[OH:2][C:3]1[CH:12]=[C:11]2[C:6]([C@H:7]([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][N:28]4[CH2:32][CH2:31][CH2:30][CH2:29]4)=[CH:21][CH:20]=3)[C@H:8]([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:9][O:10]2)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 1049PyridineHCID 21453333382-06-8

Product 1

HCID 70113588HCID 70113588, compound

Reagents, catalysts & solvents 1

HCID 69401Einecs 211-027-4Solvent

Conditions

Temperature
140 °C

Procedure

cis-7-Methoxy-3-phenyl-4-{4-[2-(pyrrolidin-1-yl)ethoxy]phenyl}chromane (4 g) was dissolved in melted pyridinium chloride, prepared from a mixture of pyridine (20 ml) and conc. hydrochloric acid (21 ml) where the water was removed by distillation at 140° C. The mixture was heated at 140° C. for 3 hours and then at 150° C. for 6 hours. The mixture was cooled down to 100° C. Water was added (30 ml) and the mixture was cooled down to 30° C. Toluene (30 ml) and sodium hydroxide (32,5%) to pH 12 was added. The mixture emulsified and was again made pH 3 with conc. hydrochloric acid. The hydrochloride of cis-7-hydroxy-3-phenyl-4-{4-[2-(pyrrolidin-1-yl)ethoxy]phenyl}chromane precipitated as a sticky product. It was dissolved in ethanol (200 ml) and water (10 ml), treated with active carbon, filtered and evaporated. Redissolved in ethanol (50 ml) and water until dissolved at 79° C. The product crystallised when the solution was cooled down to room temperature.

Workup

  1. customwas removed by distillation at 140° C
  2. temperatureThe mixture was cooled down to 100° C
  3. additionWater was added (30 ml)
  4. temperaturethe mixture was cooled down to 30° C
  5. additionToluene (30 ml) and sodium hydroxide (32,5%) to pH 12 was added
  6. customThe hydrochloride of cis-7-hydroxy-3-phenyl-4-{4-[2-(pyrrolidin-1-yl)ethoxy]phenyl}chromane precipitated as a sticky product
  7. dissolutionIt was dissolved in ethanol (200 ml)
  8. additionwater (10 ml), treated with active carbon
  9. filtrationfiltered
  10. customevaporated
  11. dissolutionRedissolved in ethanol (50 ml)
  12. dissolutionwater until dissolved at 79° C
  13. customThe product crystallised when the solution
  14. temperaturewas cooled down to room temperature

Sources & evidence

ORD record
ord-caf0fe9fd68a4a2baaf8961a4cdd4b18
Source dataset
uspto-grants-2001_11
Patent number
US06316494B1

Reaction notes

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