Sodium Carbonate → HCID 10315567, compound

HRID 2301199Notes

Reaction equation

HRID 2301199 reaction equation
N([O-])=O.[Na+].N[C:6]1[CH:29]=[CH:28][C:9]2[C:10]([CH2:13][CH2:14][CH:15]3[CH2:20][CH2:19][N:18]([CH2:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[CH2:17][CH2:16]3)=[N:11][O:12][C:8]=2[CH:7]=1.C([O-])([O-])=O.[Na+].[Na+].[C:36]([Cu])#[N:37]>O.Cl.C1(C)C=CC=CC=1>[C:36]([C:6]1[CH:29]=[CH:28][C:9]2[C:10]([CH2:13][CH2:14][CH:15]3[CH2:20][CH2:19][N:18]([CH2:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[CH2:17][CH2:16]3)=[N:11][O:12][C:8]=2[CH:7]=1)#[N:37]

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 9945661HCID 9945661, compoundHCID 23668193Sodium NitriteHCID 178418546HCID 178418546, compound

Product 1

HCID 10315567HCID 10315567, compoundYield 43%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

A solution of NaNO2 (0.112 g, 1.62 mmol) in H2O (4 mL) was added to a solution of 6-amino-3-[2-[1-(phenylmethyl)-4-piperidinyl]ethyl]-1,2-benzisoxazole (0.534 g, 1.59 mmol) in 28% HCl (20 mL) kept at 0° C. The resulting mixture was neutralized to pH 7 by cautious addition of solid Na2CO3. The neutral mixture was added in portions to a well-stirred mixture of toluene (75 mL), ice, and a freshly prepared solution of CuCN (Organic Synthesis, Coll. Vol. I, p. 514; CuSO4: 0.318 g, 1.99 mmol). The mixture obtained was kept at 0° C. for 30 minutes, then at room temperature for 2 hours, and finally, heated at 50° C. for 5 minutes. The mixture was extracted with ethyl acetate and the organic phase was washed with H2O, brine, dried (MgSO4), filtered, and concentrated. Purification by silica gel flash chromatography (3% MeOH—CH2Cl2) gave the title compound (0.236 g, 43%) as a pale orange solid. Recrystallization (EtOH-hexanes) of a small sample gave the title compound as an off-white solid.

Workup

  1. customkept at 0° C
  2. customThe mixture obtained
  3. waitat room temperature for 2 hours
  4. extractionThe mixture was extracted with ethyl acetate
  5. washthe organic phase was washed with H2O, brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification by silica gel flash chromatography (3% MeOH—CH2Cl2)

Sources & evidence

ORD record
ord-642708f089fa4e279e8bb7b2e65d4f62
Source dataset
uspto-grants-2002_12
Patent number
US06498255B2

Reaction notes

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