Methylamine → N-{2-methoxy-5-(5-trifluromethyltetrazole-1-yl)benzyl}-N-methylamine

HRID 1436912Notes

Reaction equation

HRID 1436912 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:8]([N:11]2[C:15]([C:16]([F:19])([F:18])[F:17])=[N:14][N:13]=[N:12]2)=[CH:7][C:4]=1[CH:5]=O.[CH3:20][NH2:21]>ClCCl.C(O)C.C(O)(=O)C>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:8]([N:11]2[C:15]([C:16]([F:19])([F:18])[F:17])=[N:14][N:13]=[N:12]2)=[CH:7][C:4]=1[CH2:5][NH:21][CH3:20]

Participants

6

Reactant 2

HCID 6329MethylamineHCID 113916182-Methoxy-5-[5-(trifluoromethyl)tetrazol-1-yl]benzaldehyde

Product 1

HCID 57939583N-{2-methoxy-5-(5-trifluromethyltetrazole-1-yl)benzyl}-N-methylamine

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

In 40 ml of dichloromethane was dissolved 2.72 g of 2-methoxy-5-(5-trifluoromethyltetrazole-1-yl)benzaldehyde, and added thereto was 2.5 ml of 8 M methylamine in ethanol solution, 0.572 ml of acetic acid and 3.12 g of triacetoxy sodium borohydride, the mixture was stirred at room temperature for 6 hours. The reaction mixture was washed with saturated aqueous sodium hydrocarbonate solution, and the organic layers were dried and concentrate. The residue was purified by silica gel column chromatography (chloroform:methanol=49:1 to 4:1), to give 2.2 g of N-{2-methoxy-5-(5-trifluromethyltetrazole-1-yl)benzyl}-N-methylamine as shown in Table 136 below.

Workup

  1. additionadded
  2. washThe reaction mixture was washed with saturated aqueous sodium hydrocarbonate solution
  3. customthe organic layers were dried
  4. concentrationconcentrate
  5. customThe residue was purified by silica gel column chromatography (chloroform:methanol=49:1 to 4:1)

Sources & evidence

ORD record
ord-373822fbb2184dc4954c487e35f9615f
Source dataset
uspto-grants-2009_11
Patent number
US07619092B2

Reaction notes

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