Acetaldehyde, 2,2-dimethoxy- → N-methyl-N-(4-nitrophenylmethyl)-2,2-dimethoxy-ethylamine

HRID 1157690Notes

Reaction equation

HRID 1157690 reaction equation
[CH3:1][NH:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][CH:5]=1.[CH3:13][O:14][CH:15]([O:18][CH3:19])[CH:16]=O.C([BH3-])#N.[Na+]>C1COCC1.C(OC)(C)(C)C.O.C(O)(=O)C>[CH3:1][N:2]([CH2:16][CH:15]([O:18][CH3:19])[O:14][CH3:13])[CH2:3][C:4]1[CH:5]=[CH:6][C:7]([N+:10]([O-:12])=[O:11])=[CH:8][CH:9]=1

Participants

8

Reactant 3

HCID 162650Acetaldehyde, 2,2-dimethoxy-HCID 409440N-methyl-1-(4-nitrophenyl)methanamineHCID 5003444Sodium cyanoborohydride

Product 1

HCID 68643690N-methyl-N-(4-nitrophenylmethyl)-2,2-dimethoxy-ethylamine

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

A mixture of 1.56 g N-methyl-N-(4-nitrobenzyl)amine in 40 ml THF is combined with 2.85 ml of a 45% solution of 2,2-dimethoxyacetaldehyde in tert.-butylmethylether. Then 24 mg of p-TsOHx H2O and 1.12 ml glacial acetic acid are added and the mixture is stirred for 2 h. Then 1.81 g of sodium cyanoborohydride are added batchwise and the mixture is stirred for another 2 h. 5 ml of water are added to the mixture, then it is evaporated down to approx. 30% of the volume, the residue is combined with water and extracted 3× with EtOAc. The combined organic phases are dried with Na2SO4, concentrated and the crude product is purified by chromatography (Alox; petroleum ether/EtOAc 8/2->7/3).

Workup

  1. stirringthe mixture is stirred for another 2 h
  2. customit is evaporated down to approx. 30% of the volume
  3. extractionextracted 3× with EtOAc
  4. dry with materialThe combined organic phases are dried with Na2SO4
  5. concentrationconcentrated
  6. customthe crude product is purified by chromatography (Alox; petroleum ether/EtOAc 8/2->7/3)

Sources & evidence

ORD record
ord-22652489a8dd447b9bb6a2b206d2e239
Source dataset
uspto-grants-2010_10
Patent number
US07807693B2

Reaction notes

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