Hydrochloric Acid → M-58996

HRID 967787Notes

Reaction equation

HRID 967787 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][N:11]2[CH2:16][CH2:15][C:14]([CH2:18][N:19]([CH3:33])[C:20]3[CH:32]=[CH:31][C:23]([C:24]([O:26]C(C)(C)C)=[O:25])=[CH:22][CH:21]=3)([OH:17])[CH2:13][CH2:12]2)=[CH:5][CH:4]=1)#[N:2].O.C(=O)([O-])[O-].[K+].[K+].[ClH:41]>>[ClH:41].[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][N:11]2[CH2:12][CH2:13][C:14]([CH2:18][N:19]([CH3:33])[C:20]3[CH:21]=[CH:22][C:23]([C:24]([OH:26])=[O:25])=[CH:31][CH:32]=3)([OH:17])[CH2:15][CH2:16]2)=[CH:7][CH:8]=1)#[N:2]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 11430Potassium CarbonateHCID 22930217Tert-butyl 4-({1-[2-(4-cyanophenyl)ethyl]-4-hydroxypiperidin-4-ylmethyl}methylamino)benzoate

Product 1

HCID 67371796M-58996

Procedure

The compound (100 mg) obtained in Step 2 of Example 21 was dissolved in 6N hydrochloric acid (0.5 mL) at room temperature and stirred at the same temperature for five hours. To the mixture was added water (3 mL) and adjusted to pH 9 to 10 by potassium carbonate, and the aqueous layer was washed with ethyl acetate. Insoluble matter of the aqueous layer was removed by filtration and the filtrate was adjusted to pH 3 with 6N hydrochloric acid. The precipitate was collected by filtration and dried to obtain the titled compound (71 mg) as crystals. The physical data of the obtained compound accord with those of the compound of Example 29.

Workup

  1. washthe aqueous layer was washed with ethyl acetate
  2. customInsoluble matter of the aqueous layer was removed by filtration
  3. filtrationThe precipitate was collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-73f1b51b37c54a48a8b1e71ce9bc6bd0
Source dataset
uspto-grants-2005_10
Patent number
US06956046B2

Reaction notes

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