Sodium Carbonate → HCID 89923867, compound

HRID 1752650Notes

Reaction equation

HRID 1752650 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([N:7]2[CH2:12][CH2:11][N:10]([C:13]#[N:14])[CH2:9][CH2:8]2)[CH2:3][CH2:2]1.Cl.[NH2:16][OH:17].C([O-])([O-])=O.[Na+].[Na+]>C(O)C>[OH:17]/[N:16]=[C:13](\[N:10]1[CH2:11][CH2:12][N:7]([CH:4]2[CH2:5][CH2:6][O:1][CH2:2][CH2:3]2)[CH2:8][CH2:9]1)/[NH2:14]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 89923787HCID 89923787, compound

Product 1

HCID 89923867HCID 89923867, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 4-(tetrahydro-2H-pyran-4-yl)piperazine-1-carbonitrile (632 mg, 3.24 mmol), Ethanol (10 mL), hydroxylamine hydrochloric acid (257 mg, 3.70 mmol) and Na2CO3 (785 mg, 7.40 mmol) was heated to 80° C. After 1.5 h, the solids were filtered off and the filtrate concentrated in vacuo. The residue was dissolved into a minimum amount of methanol and treated with 5 mL of 1 M of HCl/Ether and diluted by acetone. Resulting solids were collected and dried in vacuo to afford the title compound (566 mg, 1.879 mmol, 76% yield) as white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm=11.88 (br. s., 4H), 11.20 (br. s., 1H), 10.17 (br. s., 1H), 8.26 (br. s., 2H), 4.09-3.87 (m, 5H), 3.69-3.49 (m, 4H), 3.42 (br. s., 1H), 3.26 (t, J=11.5 Hz, 2H), 3.17-2.98 (m, 2H), 2.00 (d, J=11.1 Hz, 2H), 1.83-1.64 (m, 2H); LC/MS (m/z) ES+ (ELSD)=229.2 (M+1).

Workup

  1. filtrationthe solids were filtered off
  2. concentrationthe filtrate concentrated in vacuo
  3. dissolutionThe residue was dissolved into a minimum amount of methanol
  4. additiontreated with 5 mL of 1 M of HCl/Ether
  5. additiondiluted by acetone
  6. customResulting solids
  7. customwere collected
  8. customdried in vacuo

Sources & evidence

ORD record
ord-f3132cfeb48b462c8070536a731af128
Source dataset
uspto-grants-2015_10
Patent number
US09163023B2

Reaction notes

Loading…