Hydrazine → Hydrochloric Acid

HRID 578919Notes

Reaction equation

HRID 578919 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([NH:8][CH2:9][CH:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)=[O:7])=[CH:4][N:3]=1.[NH2:18][NH2:19]>C(O)(C)C>[NH:18]([C:2]1[CH:17]=[CH:16][C:5]([C:6]([NH:8][CH2:9][CH:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)=[O:7])=[CH:4][N:3]=1)[NH2:19].[ClH:1]

Participants

5

Reactant 2

HCID 9321HydrazineHCID 552088446-chloro-N-((tetrahydro-2H-pyran-4-yl)methyl)nicotinamide

Product 2

HCID 313Hydrochloric AcidYield 271.7%HCID 637057936-hydrazinyl-N-((tetrahydro-2H-pyran-4-yl)methyl)nicotinamide

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
20 °C

Procedure

Combined 6-chloro-N-((tetrahydro-2 H-pyran-4-yl)methyl)nicotinamide (828 mg, 3.25 mmol) and hydrazine (0.510 mL, 16.25 mmol) in isopropanol (10 mL) and heated at 80° C. for 22 h. Cool to 20° C. and after 2 days a white precipitate formed and was collected by filtration, rinsed with isopropanol, and dried under vacuum to give the title compound as its HCl salt (322 mg) as a white solid. A second crop was collected from the filtrate (500 mg). The combined yield was 822 mg (88%). MS m/z 251 [M+H]+. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.09-1.26 (m, 2 H) 1.57 (dd, J=12.9, 1.8 Hz, 2 H) 1.75 (dtt, J=14.9, 7.5, 7.5, 3.4, 3.4 Hz, 1 H) 3.11 (t, J=6.3 Hz, 2 H) 3.19-3.31 (m, 2 H) 3.83 (dd, J=11.4, 2.5 Hz, 2 H) 4.26 (br. s., 2 H) 6.68 (d, J=8.8 Hz, 1 H) 7.87 (dd, J=8.8, 2.3 Hz, 1 H) 7.97 (s, 1 H) 8.18 (t, J=5.7 Hz, 1 H) 8.49 (d, J=1.8 Hz, 1 H).

Workup

  1. customformed
  2. filtrationwas collected by filtration
  3. washrinsed with isopropanol
  4. customdried under vacuum

Sources & evidence

ORD record
ord-1d2861f7bdcf47b58141f891f2ae7e81
Source dataset
uspto-grants-2015_05
Patent number
US09040522B2

Reaction notes

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