Acetone → HCID 69018361, compound

HRID 491603Notes

Reaction equation

HRID 491603 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][C:3]=1[O:4][CH2:5][CH:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1.[CH3:19][C:20]([CH3:22])=O.[BH3-]C#N.[Na+]>CC#N>[Cl:1][C:2]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][C:3]=1[O:4][CH2:5][CH:6]1[CH2:7][CH2:8][N:9]([CH:20]([CH3:22])[CH3:19])[CH2:10][CH2:11]1

Participants

5

Reactant 3

HCID 180AcetoneHCID 5003444Sodium cyanoborohydrideHCID 63990969HCID 63990969, compound

Product 1

HCID 69018361HCID 69018361, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-(2-Chloro-5-nitro-phenoxymethyl)-piperidine (7 g, 25.9 mmol) was dissolved in CH3CN (50 mL) and acetone (9.48 ml, 129 mmol) was added. NaBH3CN (2.6 g, 41.4 mmol) was added. After 14 h, the mixture was concentrated in vacuo and the residue was dissolved in EtOAc, washed with brine. The EtOAc portion was dried with Na2SO4, and evaporated. The title compound was purified by column chromatography using 0-75% of a 90:10:1 (CH2Cl2:MeOH: NH4OH) solution as the eluent to yield a yellow solid. MS(MH+)=NA; Calc'd 312.12 for C15H21ClN2O3.

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. dissolutionthe residue was dissolved in EtOAc
  3. washwashed with brine
  4. dry with materialThe EtOAc portion was dried with Na2SO4
  5. customevaporated
  6. customThe title compound was purified by column chromatography
  7. customto yield a yellow solid

Sources & evidence

ORD record
ord-79f4bad5d75644c1934e0fa3a6835e35
Source dataset
uspto-grants-2009_05
Patent number
US07531553B2

Reaction notes

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