Methylamine → N-Methyl-N-naphthylmethylamine

HRID 893992Notes

Reaction equation

HRID 893992 reaction equation
Cl[CH2:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1.[CH3:13][NH2:14]>C(O)C>[CH3:13][NH:14][CH2:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 68451-Chloromethylnaphthalene

Product 1

HCID 84474N-Methyl-N-naphthylmethylamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

17.6 g of 1-chloromethyl-naphthalene in 40 ml of absolute ethanol is added, dropwise, at 0° to 5°, to 100 ml of a 33% solution of methylamine in absolute ethanol. The mixture is allowed to stand overnight and is then evaporated. The residue is taken up in a little chloroform and washed with 100 ml of 1 N sodium hydroxide solution and with water. The organic phase is dried and evaporated to dryness. The residue is distilled at 0.01 Torr to obtain the heading compound as main fraction, b.p. 85°-87°.

Workup

  1. customat 0° to 5°
  2. customis then evaporated
  3. washwashed with 100 ml of 1 N sodium hydroxide solution and with water
  4. customThe organic phase is dried
  5. customevaporated to dryness
  6. distillationThe residue is distilled at 0.01 Torr
  7. customto obtain the heading compound as main fraction, b.p. 85°-87°

Sources & evidence

ORD record
ord-be20ca3302fa4fb6bd3a91c49836586f
Source dataset
uspto-grants-1981_08
Patent number
US04282251

Reaction notes

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