Hydrochloric Acid → 1346528-51-5

HRID 1429677Notes

Reaction equation

HRID 1429677 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[NH:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([CH2:17][C:18]2[CH:28]=[CH:27][C:21]3[O:22][C:23]([F:26])([F:25])[O:24][C:20]=3[CH:19]=2)[CH2:13][CH2:12]1)=[O:10].[ClH:29]>C(O)C>[ClH:1].[ClH:29].[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[NH:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([CH2:17][C:18]2[CH:28]=[CH:27][C:21]3[O:22][C:23]([F:26])([F:25])[O:24][C:20]=3[CH:19]=2)[CH2:13][CH2:12]1)=[O:10]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 54576693JNJ-42165279

Product 1

HCID 545766941346528-51-5Yield 72%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

A solution consisting of 4-(2,2-difluoro-benzo[1,3]dioxol-5-ylmethyl)-piperazine-1-carboxylic acid (4-chloro-pyridin-3-yl)-amide (5.0 g, 12 mmol) and ethanol (200 mL) was treated with saturated aqueous HCl (3.0 mL, 3 equiv). The solvent was removed in vacuo, ethanol (100 mL) was added and the suspension was cooled to 0° C. and filtered. The resulting white solid was rinsed with cold ethanol (25 mL) and dried under vacuum to give 4-(2,2-difluoro-benzo[1,3]dioxol-5-ylmethyl)-piperazine-1-carboxylic acid (4-chloro-pyridin-3-yl)-amide bis-hydrochloride (4.25 g, 72%). 1H NMR (400 MHz, DMSO) δ 11.61 (br s, 1H), 8.98 (s, 1H), 8.65 (s, 1H), 8.37 (d, J=5.4 Hz, 1H), 7.78 (d, J=1.4 Hz, 1H), 7.69 (d, J=5.4 Hz, 1H), 7.52 (d, J=8.3 Hz, 1H), 7.46 (dd, J=8.3, 1.5 Hz, 1H), 4.39 (s, 2H), 4.28-4.12 (m, 2H), 3.49-3.26 (m, 4H), 3.03 (s, 2H).

Workup

  1. customThe solvent was removed in vacuo, ethanol (100 mL)
  2. additionwas added
  3. filtrationfiltered
  4. washThe resulting white solid was rinsed with cold ethanol (25 mL)
  5. customdried under vacuum

Sources & evidence

ORD record
ord-572d00f90b07416e9d04461afd5721f2
Source dataset
uspto-grants-2015_01
Patent number
US08940745B2

Reaction notes

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