Hydrochloric Acid → HCID 86724051, compound

HRID 1753768Notes

Reaction equation

HRID 1753768 reaction equation
[CH3:1][C:2]1[CH:17]=[CH:16][C:5]([O:6][CH2:7][CH2:8][CH2:9][N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)=[CH:4][C:3]=1[N+:18]([O-])=O.Cl[Sn]Cl.O.Cl>CCO>[CH3:1][C:2]1[CH:17]=[CH:16][C:5]([O:6][CH2:7][CH2:8][CH2:9][N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)=[CH:4][C:3]=1[NH2:18]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 43835034Tin dichloride dihydrateHCID 71240398HCID 71240398, compound

Product 1

HCID 86724051HCID 86724051, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of the 4-[3-(4-methyl-3-nitro-phenoxy)-propyl]-morpholine V-i (350 mg, 1.25 mmol) in 90% EtOH (15 mL) was treated with SnCl2.H2O (1.58 g, 6.24 mmol) and conc. HCl (1.04 mL, 12.5 mmol) and heated to reflux for 1 h. The cooled solution was concentrated under reduced pressure and taken to pH=8 with a saturated solution of NaHCO3 then extracted with EtOAc. The combined organics were dried (MgSO4), filtered and evaporated to the desired product V-g as a viscous yellow oil (306 mg, 98%). 1H NMR (300 MHz, CDCl3) δ 6.92 (d, J=8.8 Hz, 1H), 6.30-6.24 (m, 2H), 3.96 (t, J=6.3 Hz, 2H), 3.76-3.69 (m, 4H), 3.58 (s, 2H), 2.57-2.42 (m, 6H), 2.09 (s, 3H), 1.93 (dt, J=13.3, 6.5 Hz, 3H).

Workup

  1. temperatureheated
  2. temperatureto reflux for 1 h
  3. concentrationThe cooled solution was concentrated under reduced pressure
  4. extractionthen extracted with EtOAc
  5. dry with materialThe combined organics were dried (MgSO4)
  6. filtrationfiltered
  7. customevaporated to the desired product V-g as a viscous yellow oil (306 mg, 98%)

Sources & evidence

ORD record
ord-81133e7f0a9d4d51877107a0b496e48e
Source dataset
uspto-grants-2015_10
Patent number
US09168245B2

Reaction notes

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