Sodium Cyanate → HCID 15295463, compound

HRID 2210547Notes

Reaction equation

HRID 2210547 reaction equation
[CH:1]1([CH2:6][C:7]2[CH:8]=[C:9]([CH:15]3[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.[O-:21][C:22]#[N:23].[Na+]>C(O)(=O)C.O>[CH:1]1([CH2:6][C:7]2[CH:8]=[C:9]([CH:15]3[CH2:16][CH2:17][N:18]([C:22]([NH2:23])=[O:21])[CH2:19][CH2:20]3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 2

HCID 517096Sodium CyanateHCID 19379065HCID 19379065, compound

Product 1

HCID 15295463HCID 15295463, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To a stirred solution of 4-(3-cyclopentylmethyl-4-methoxyphenyl)piperidine (1.8 mmol, 0.500 g) in acetic acid (5 mL) was added a solution of sodium cyanate (10.8 mmol, 0.702 g) in water (15 mL) dropwise over 20 minutes at room temperature. The resulting solution was stirred at room temperature overnight, after which the acetic acid was removed in vacuo. The residue was partitioned between EtOAc (200 mL) and H2O (200 mL). The aqueous phase was extracted with EtOAc (1×200 mL), the combined organics dried (Na2SO4), concentrated in vacuo and purified by flash chromatography (SiO2 ; EtOAc) to give the title compound as a white solid, mp=168°-169° C. (0.5 mmol, 1.054 g, 27%).

Workup

  1. customafter which the acetic acid was removed in vacuo
  2. customThe residue was partitioned between EtOAc (200 mL) and H2O (200 mL)
  3. extractionThe aqueous phase was extracted with EtOAc (1×200 mL)
  4. dry with materialthe combined organics dried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. custompurified by flash chromatography (SiO2 ; EtOAc)

Sources & evidence

ORD record
ord-bf5c99d08397400db37a56ba16095f57
Source dataset
uspto-grants-1995_10
Patent number
US05459151

Reaction notes

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