Benzocaine → Ethyl 4-[3-(1-naphthyloxy)propylamino]benzoate

HRID 443646Notes

Reaction equation

HRID 443646 reaction equation
[C:1]1([O:11][CH2:12][CH2:13][CH2:14]Br)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[NH2:16][C:17]1[CH:27]=[CH:26][C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:19][CH:18]=1>CN(C)P(N(C)C)(N(C)C)=O>[C:1]1([O:11][CH2:12][CH2:13][CH2:14][NH:16][C:17]2[CH:18]=[CH:19][C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:26][CH:27]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 2337BenzocaineHCID 129593811-(3-Bromopropoxy)naphthalene

Product 1

HCID 23468296Ethyl 4-[3-(1-naphthyloxy)propylamino]benzoate

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Procedure

A solution of 10 g. 3-(α-naphthyloxy)propyl bromide and 12.5 g. ethyl 4-aminobenzoate in 100 ml. hexamethylphosphoramide is stirred at 110° for 15 hours. The cooled solution is diluted with 200 ml. water and extracted 3 times with 100 ml. portions of ether. The combined extracts are washed with brine, dried and evaporated to an orange residue. The product is crystallized from ethanol to yield a solid which is crystallized from ethanol to yield white crystals, m.p. 93°-94° C.

Workup

  1. additionThe cooled solution is diluted with 200 ml
  2. extractionwater and extracted 3 times with 100 ml
  3. washThe combined extracts are washed with brine
  4. customdried
  5. customevaporated to an orange residue
  6. customThe product is crystallized from ethanol
  7. customto yield a solid which
  8. customis crystallized from ethanol
  9. customto yield white crystals, m.p. 93°-94° C.

Sources & evidence

ORD record
ord-9ece08b102634e3fbc962c62d08e8e8b
Source dataset
uspto-grants-1981_04
Patent number
US04260816

Reaction notes

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