Formaldehyde → HCID 69021578, compound

HRID 491602Notes

Reaction equation

HRID 491602 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.C=O.[BH3-][C:22]#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]([CH3:22])[CH2:10][CH2:11]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 63990969HCID 63990969, compound

Product 1

HCID 69021578HCID 69021578, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-(2-Chloro-5-nitro-phenoxymethyl)-piperidine (4 g, 14.8 mmol) was dissolved in CH3CN (20 ml), and formaldehyde (5.9 ml, 37% aqueous) and NaBH3CN (1.49 g, 23.68 mmol) were added. After 4 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 284.09 for C13H17ClN2O3.

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-2c53492ef35449d0a7b837571a733280
Source dataset
uspto-grants-2009_05
Patent number
US07531553B2

Reaction notes

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