Sodium Hydroxide → N-[4-Chloro-3-(2-dimethylaminoethoxy)phenyl]aminoacetaldehyde dimethyl acetal

HRID 1419820Notes

Reaction equation

HRID 1419820 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[O:9][CH2:10][CH2:11][N:12]([CH3:14])[CH3:13].[CH3:15][O:16][CH:17]([O:20][CH3:21])[CH:18]=O.CC(OC)(C)C.C([BH3-])#N.[Na+].[OH-].[Na+]>CO.C(O)(=O)C>[CH3:15][O:16][CH:17]([O:20][CH3:21])[CH2:18][NH:6][C:5]1[CH:7]=[CH:8][C:2]([Cl:1])=[C:3]([O:9][CH2:10][CH2:11][N:12]([CH3:14])[CH3:13])[CH:4]=1

Participants

8

Reactant 5

HCID 14798Sodium HydroxideHCID 15413tert-Butyl methyl etherHCID 162650Acetaldehyde, 2,2-dimethoxy-HCID 5003444Sodium cyanoborohydrideHCID 121354204-Chloro-3-(2-dimethylamino-ethoxy)aniline

Product 1

HCID 57027129N-[4-Chloro-3-(2-dimethylaminoethoxy)phenyl]aminoacetaldehyde dimethyl acetalYield 87%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

To a suspension of 4-chloro-3-(2-dimethylaminoethoxy)aniline (1.22 g, 0.006 mol) in MeOH (30 ml) containing dimethoxyethanal in MTBE (1.76 g, 0.17 mol) and glacial acetic acid (1.71 g) was added sodium cyanoborohydride (1.78 g, 0.03 mol ) portionwise at 0° C. The reaction was left to stir at room temperature for 1 hour, and then 10% aq. NaOH was added and the mixture was extracted with CH2Cl2. The combined organic layers were dried (Na2SO4), and concentrated in vacuo to give a brown oil. Purification by FCC, eluting with CH2Cl2 gave the title compound (1.49 g, 87%)

Workup

  1. waitThe reaction was left
  2. extractionthe mixture was extracted with CH2Cl2
  3. dry with materialThe combined organic layers were dried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customto give a brown oil
  6. customPurification by FCC
  7. washeluting with CH2Cl2

Sources & evidence

ORD record
ord-1d2e122cd4584aa393c74679c098e8fe
Source dataset
uspto-grants-1999_03
Patent number
US05889022

Reaction notes

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