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

HRID 1833380Notes

Reaction equation

HRID 1833380 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

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 temperature was maintained at 40°-50° C
  7. temperatureThe solution was then refluxed for 15 minutes
  8. additiondiluted with water (1.5 l.)
  9. extractionthe aqueous mixture extracted with ether (3 × 200ml.)
  10. washThe combined ethereal extracts were washed with water (2 × 100 ml.)
  11. dry with materialdried (K2CO3)
  12. customevaporated

Sources & evidence

ORD record
ord-dd5fc98546be47a7b2453dc21b9341cb
Source dataset
uspto-grants-1978_01
Patent number
US04066651

Reaction notes

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