4-Chlorobenzaldehyde → HCID 28684408, compound

HRID 408592Notes

Reaction equation

HRID 408592 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][C:5](=[O:7])[CH3:6].C([O-])(O)=O.[Na+].[Cl:13][C:14]1[CH:21]=[CH:20][C:17]([CH:18]=O)=[CH:16][CH:15]=1.[BH4-].[Na+]>CO>[Cl:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18][NH:1][CH2:2][CH2:3][NH:4][C:5](=[O:7])[CH3:6])=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 77264-ChlorobenzaldehydeHCID 66082N-(2-aminoethyl)acetamideHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydride

Product 1

HCID 28684408HCID 28684408, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of N-(2-amino-ethyl)-acetamide (1.2 eq.) in MeOH were added NaHCO3 (1.5 eq.) and 4-chlorobenzaldehyde (1 eq.). The reaction was refluxed for 4 h, then cooled to 0° C. NaBH4 (1.2 eq.) was added portionwise. The reaction was stirred for 1 h at 0° C., then 15 h at 20° C. The crude was concentrated under reduced pressure then partitioned between water and DCM. The aqueous layer was then extracted twice with DCM. The organic layers were combined, dried over MgSO4, filtered and concentrated under reduced pressure. The crude was purified by chromatography on silica gel (elution with heptane/EtOAc: 1/0 to 0/1) to afford N-[2-(4-chloro-benzylamino)-ethyl]-acetamide.

Workup

  1. temperatureThe reaction was refluxed for 4 h
  2. custom15 h
  3. customat 20° C
  4. concentrationThe crude was concentrated under reduced pressure
  5. customthen partitioned between water and DCM
  6. extractionThe aqueous layer was then extracted twice with DCM
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe crude was purified by chromatography on silica gel (elution with heptane/EtOAc: 1/0 to 0/1)

Sources & evidence

ORD record
ord-d2e705cb6e6349209f47db9c89b5a911
Source dataset
uspto-grants-2014_06
Patent number
US08759334B2

Reaction notes

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