HCID 44464173, compound → HCID 44464686, compound

HRID 453268Notes

Reaction equation

HRID 453268 reaction equation
C[O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][C:7]([N:13]1[C:17]([CH3:18])=[CH:16][C:15]([O:19][CH2:20][CH2:21][N:22]3[CH2:27][CH2:26][O:25][CH2:24][CH2:23]3)=[N:14]1)=[CH:8]2>Cl>[OH:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][C:7]([N:13]1[C:17]([CH3:18])=[CH:16][C:15]([O:19][CH2:20][CH2:21][N:22]3[CH2:27][CH2:26][O:25][CH2:24][CH2:23]3)=[N:14]1)=[CH:8]2

Participants

3

Reactant 1

HCID 44464173HCID 44464173, compound

Product 1

HCID 44464686HCID 44464686, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 4-{2-[1-(5-methoxynaphthalen-2-yl)-5-methyl-1H-pyrazol-3-yloxy]ethyl}morpholine (400 mg, 1.08 mmol) in HCl conc. (25 ml) was heated at 90° C. during 7 hrs, cooled down, and evaporated to dryness in a rotavapor. A remaining crude of 4-{2-[1-(5-hydroxynaphthalen-2-yl)-5-methyl-1H-pyrazol-3-yloxy]ethyl}morpholine chlorhydrate was left, which was crystallized in isopropyl alcohol-petroleum ether obtaining 0.32 g (76%) of the product in a solid amorphous form with a melting point m.p.<70° C., and highly hygroscopic.

Workup

  1. temperaturecooled down
  2. customevaporated to dryness in a rotavapor
  3. waitA remaining crude of 4-{2-[1-(5-hydroxynaphthalen-2-yl)-5-methyl-1H-pyrazol-3-yloxy]ethyl}morpholine chlorhydrate was left
  4. customwhich was crystallized in isopropyl alcohol-petroleum ether obtaining 0.32 g (76%) of the product in a solid amorphous form with a melting point m.p.<70° C.

Sources & evidence

ORD record
ord-7d822d7070da41f28722993d0fdc4f01
Source dataset
uspto-grants-2013_07
Patent number
US08492425B2

Reaction notes

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