Sodium Bicarbonate → HCID 178527275, compound

HRID 1711422Notes

Reaction equation

HRID 1711422 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([O:14][C:15]2[CH:20]=[CH:19][C:18]([NH2:21])=[C:17]([CH2:22][S:23]([C:26]3[C:35]4[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=4)[CH:29]=[CH:28][CH:27]=3)(=[O:25])=[O:24])[CH:16]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:36]([O-])=O.[Na+].C(=O)(O)[O-].[Na+]>C1COCC1.Cl.O>[CH2:1]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([O:14][C:15]2[CH:16]=[C:17]3[C:18](=[CH:19][CH:20]=2)[NH:21][N:36]=[C:22]3[S:23]([C:26]2[C:35]3[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=3)[CH:29]=[CH:28][CH:27]=2)(=[O:25])=[O:24])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 516892Sodium BicarbonateHCID 23668193Sodium NitriteHCID 588286234-(1-Benzylpiperidin-3-yloxy)-2-(1-naphthylsulfonylmethyl)phenylamine

Product 1

HCID 178527275HCID 178527275, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-(1-benzylpiperidin-3-yloxy)-2-(1-naphthylsulfonylmethyl)phenylamine (1.0 g, 2 mmoles) in THF and 4M HCl (10 mL), under nitrogen, at 3° C. was treated dropwise with a solution of sodium nitrite (0.16 g, 2.4 mmoles) in H2O, poured into a cold solution of saturated sodium bicarbonate and extracted with EtOAc. The extracts were combined, dried over Na2SO4, and concentrated under vacuum to afford the title compound as an off white solid (0.7 g, 1.4 mmoles).

Workup

  1. extractionextracted with EtOAc
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-137168122da04461a5803aaf6be7fd70
Source dataset
uspto-grants-2010_09
Patent number
US07790751B2

Reaction notes

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