Water → Benzenemethanamine, 2-chloro-N-(4-methoxyphenyl)-

HRID 1390286Notes

Reaction equation

HRID 1390286 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[CH3:10][O:11][C:12]1[CH:18]=[CH:17][C:15]([NH2:16])=[CH:14][CH:13]=1.O>C1(C)C=CC=CC=1>[CH3:10][O:11][C:12]1[CH:18]=[CH:17][C:15]([NH:16][CH2:4][C:3]2[CH:6]=[CH:7][CH:8]=[CH:9][C:2]=2[Cl:1])=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 962WaterHCID 69962-ChlorobenzaldehydeHCID 7732P-Anisidine

Product 1

HCID 11075784Benzenemethanamine, 2-chloro-N-(4-methoxyphenyl)-

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
45 °C

Procedure

A solution of 2-chlorobenzaldehyde (70 g.) and 4-methoxyaniline (61.5g.) in toluene (750 ml.) was refluxed under a Dean and Stark separator until no more water collected (ca. 1 hour). The toluene was evaporated in vacuo, and the residue was dissolved in methanol (1.5 l.). The methanolic solution was treated at room temperature with sodium borohydride (60 g.) added portionwise so that, with gentle cooling, the temperature was maintained at 40-50° C. The solution was then refluxed for 15 minutes, diluted with water (1.5 l.), and the aqueous mixture extracted with ether (3 × 200ml.). The combined ethereal extracts were washed with water (2 × 100 ml.), dried (K2CO3), and evaporated to give N-(4-methoxyphenyl)-2-chlorobenzylamine as a brown oil, Infra Red ν max 3400, 1618 cm.-1, which was used directly in the next stage.

Workup

  1. customcollected (ca. 1 hour)
  2. customThe toluene was evaporated in vacuo
  3. dissolutionthe residue was dissolved in methanol (1.5 l.)
  4. additionThe methanolic solution was treated at room temperature with sodium borohydride (60 g.)
  5. additionadded portionwise so that, with gentle cooling
  6. temperatureThe solution was then refluxed for 15 minutes
  7. additiondiluted with water (1.5 l.)
  8. extractionthe aqueous mixture extracted with ether (3 × 200ml.)
  9. washThe combined ethereal extracts were washed with water (2 × 100 ml.)
  10. dry with materialdried (K2CO3)
  11. customevaporated

Sources & evidence

ORD record
ord-d00992a2fa8540e7977a7d9bd6d814d9
Source dataset
uspto-grants-1979_02
Patent number
US04138490

Reaction notes

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