1-Naphthaleneacetic Acid → Trans (+/-) N-methyl-N-[2-(1-pyrrolidinyl)-1,2,3,4-tetrahydro-1-naphthyl]-1-naphthalene acetamide

HRID 654136Notes

Reaction equation

HRID 654136 reaction equation
[C:1]1([CH2:11][C:12]([OH:14])=O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[CH3:15][NH:16][CH:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:20][CH2:19][CH:18]1[N:27]1[CH2:31][CH2:30][CH2:29][CH2:28]1>>[CH3:15][N:16]([C@@H:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:20][CH2:19][C@H:18]1[N:27]1[CH2:31][CH2:30][CH2:29][CH2:28]1)[C:12](=[O:14])[CH2:11][C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 68621-Naphthaleneacetic AcidHCID 14476582N-methyl-2-(1-pyrrolidinyl)-1,2,3,4-tetrahydro-1-naphthalene amine

Product 1

HCID 14476594Trans (+/-) N-methyl-N-[2-(1-pyrrolidinyl)-1,2,3,4-tetrahydro-1-naphthyl]-1-naphthalene acetamideYield 54.9%

Procedure

Using the procedure of Step C of Example 1, 2.3 g of 1-naphthylacetic acid and 2 g of the product of Step B of Example 1 were reacted to obtain 5.3 g of crude product which was purified by chromatography on silica (methylene chloride 9-methanol 1). After crystallization from ethyl ether, 1.9 g of product melting at 117° C. were obtained which was crystallized from isopropyl ether to obtain 1.1 g of the expected product melting at 125° C.

Workup

  1. customwere reacted
  2. customto obtain 5.3 g of crude product which
  3. customwas purified by chromatography on silica (methylene chloride 9-methanol 1)
  4. customAfter crystallization from ethyl ether

Sources & evidence

ORD record
ord-140d2a5d0e4148469020e40cb7e790bb
Source dataset
uspto-grants-1992_07
Patent number
US05130329

Reaction notes

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