Hydrochloric Acid → HCID 68457700, compound

HRID 1677845Notes

Reaction equation

HRID 1677845 reaction equation
O1[C:5]2([CH2:9][CH2:8][N:7]([C@H:10]3[CH2:15][CH2:14][CH2:13][CH2:12][C@@H:11]3[O:16][CH2:17][CH2:18][C:19]3[C:24]([Cl:25])=[CH:23][CH:22]=[CH:21][C:20]=3[Cl:26])[CH2:6]2)[O:4]CC1.Cl>CC(=O)CC.O>[ClH:25].[O:4]=[C:5]1[CH2:9][CH2:8][N:7]([C@H:10]2[CH2:15][CH2:14][CH2:13][CH2:12][C@@H:11]2[O:16][CH2:17][CH2:18][C:19]2[C:24]([Cl:25])=[CH:23][CH:22]=[CH:21][C:20]=2[Cl:26])[CH2:6]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86608893HCID 86608893, compound

Product 1

HCID 68457700HCID 68457700, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of (1R,2R)/(1S,2S)-2-[1,4-dioxa-7-azaspiro[4.4]non-7-yl]-1-(2,6-dichlorophenethoxy)cyclohexane (15.85 g, 38.9 mmol, step ix) and 6M HCl aqueous solution (100 mL) in 2-butanone (400 mL) was refluxed for 16 hours. The cooled reaction mixture was diluted with water (100 mL) and the organic solvent was evaporated in vacuo. The organic layer was further diluted with water (400 mL), extracted with diethyl ether (500 mL) and with dichloromethane (2×600 mL). The combined dichloromethane extracts were dried over sodium sulfate and the solvent was evaporated in vacuo. Azeotropic distillation with toluene provided the title compound which was further dried under high vacuum for 15 min. The hydrochloride salt was crystallized by triturating in diethyl ether, the crystals were collected and recrystallized from a mixture of ethanol-diethyl ether to yield 11.85 g of pure product (77% yield), having the elemental analysis indicated in Table 1.

Workup

  1. temperaturewas refluxed for 16 hours
  2. customThe cooled reaction mixture
  3. customthe organic solvent was evaporated in vacuo
  4. additionThe organic layer was further diluted with water (400 mL)
  5. extractionextracted with diethyl ether (500 mL) and with dichloromethane (2×600 mL)
  6. dry with materialThe combined dichloromethane extracts were dried over sodium sulfate
  7. customthe solvent was evaporated in vacuo
  8. distillationAzeotropic distillation with toluene

Sources & evidence

ORD record
ord-bc323f0f12604e6f99b3f385f1678b87
Source dataset
uspto-grants-2011_08
Patent number
US08008342B2

Reaction notes

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