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

HRID 399264Notes

Reaction equation

HRID 399264 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+]>C(Cl)Cl.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 6344DichloromethaneSolvent

Procedure

To a suspension of 4-chloro-3-(2-dimethylaminoethoxy)aniline (D6, 1.22 g, 0.006 mol) in McOH (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. After addition, the reaction was left to stir at room temperature for 1 hour, and then 10% aqueous NaOH was added and the mixture was extraced with CH2Cl2 and 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 mg, 87% )

Workup

  1. additionAfter addition
  2. waitthe reaction was left
  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-1f61f5b02d284fab8831a6d026e1586c
Source dataset
uspto-grants-1998_10
Patent number
US05817833

Reaction notes

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