Water → HCID 22145721, compound

HRID 1940286Notes

Reaction equation

HRID 1940286 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:12]=[CH:13][C:14]=2[O:15][CH3:16])[CH:10]=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:17][C:18]1[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=1[NH2:20].O>C1(C)C=CC=CC=1>[Cl:17][C:18]1[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=1[NH:20][CH2:10][C:9]1[CH:12]=[CH:13][C:14]([O:15][CH3:16])=[C:7]([O:6][CH:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)[CH:8]=1

Participants

5

Reactant 3

HCID 962WaterHCID 72402-ChloroanilineHCID 27358933-Cyclopentyloxy-4-methoxybenzaldehyde

Product 1

HCID 22145721HCID 22145721, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 3-cyclopentyloxy-4-methoxybenzaldehyde (5 g) and 2-chloroaniline (2.5 mL) in toluene (60 mL) is heated at reflux under a Dean and Stark water trap for 3 hours. After concentration, the residue is dissolved in methanol (60 mL) and the stirred solution is treated at 0° C. with sodium cyanoborohydride (2.1 g). The temperature is allowed to rise to room temperature, and the stirring is continued for 2 hours, before dilution with ethyl acetate (100 mL) and washing with saline (100 mL). The organic layer is dried and concentrated, to give a brown oil. This oil is subjected to flash chromatography on silica gel, eluting with a mixture of ethyl acetate and hexane (1:4v/v), to give N-(2-chlorophenyl)-3-cyclopentyloxy-4-methoxybenzylamine (0.64 g), in the form of an oil. [Elemental analysis: C,69.5; H,6.8; N,4.1; Cl,10.6%; calculated: C,68.8; H,6.7; N,3.2; Cl,10.7%].

Workup

  1. concentrationAfter concentration
  2. dissolutionthe residue is dissolved in methanol (60 mL)
  3. additionthe stirred solution is treated at 0° C. with sodium cyanoborohydride (2.1 g)
  4. customto rise to room temperature
  5. washwashing with saline (100 mL)
  6. customThe organic layer is dried
  7. concentrationconcentrated
  8. customto give a brown oil
  9. washeluting with a mixture of ethyl acetate and hexane (1:4v/v)

Sources & evidence

ORD record
ord-c384385ce1d341a98db57e9ca4e49ceb
Source dataset
uspto-grants-1997_12
Patent number
US05698711

Reaction notes

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