Hydrochloric Acid → 2-(1,1-Dioxo-1lambda6-[1,2]thiazinan-2-yl)benzylamine hydrochloride

HRID 1372253Notes

Reaction equation

HRID 1372253 reaction equation
[O:1]=[S:2]1(=[O:16])[CH2:7][CH2:6][CH2:5][CH2:4][N:3]1[C:8]1[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=1[C:10]#[N:11].[ClH:17]>C(O)C.[Pd]>[ClH:17].[O:1]=[S:2]1(=[O:16])[CH2:7][CH2:6][CH2:5][CH2:4][N:3]1[C:8]1[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=1[CH2:10][NH2:11]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 235683982-(1,1-Dioxo-1lambda6-[1,2]thiazinan-2-yl)-benzonitrile

Product 1

HCID 674392922-(1,1-Dioxo-1lambda6-[1,2]thiazinan-2-yl)benzylamine hydrochlorideYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Intermediate 100, 2-(1,1-dioxo-1λ6-[1,2]thiazinan-2-yl)benzonitrile, (2.63 g, 11.14 mmol) was dissolved in ethanol (150 mL) and 1N HCl (13 mL). Added to this was 10% Pd—C (0.5 g) and the mixture shaken under H2 at 55 psi for 24 h. Filtration through Celite followed by concentration gave the title compound as a white solid (2.93 g, 95% yield). 1H-NMR (300 MHz, CD3OD) δ ppm: 7.61–7.47 (4H, m), 4.30 (2H, q, J=13.7 Hz), 3.96–3.87 (1H, m), 3.49–3.36 (3H, m), 2.40–2.31 (2H, m), 2.05–1.96 (2H, m). LCMS [M+H]+ calcd for C11H17N2SO2: 241.10. found: 241.10.

Workup

  1. filtrationFiltration through Celite
  2. concentrationfollowed by concentration

Sources & evidence

ORD record
ord-4a20fc084dba4091a3efb2e66b5bd09c
Source dataset
uspto-grants-2007_01
Patent number
US07157447B2

Reaction notes

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