(4-Nitrophenyl)acetic acid → Trans (+/-) N-methyl-4-nitro-N-[2(1-pyrrolidinyl)-1,2,3,4-tetrahydro-1-naphthyl]-benzene acetamide

HRID 654135Notes

Reaction equation

HRID 654135 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([OH:13])=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH3:14][NH:15][CH:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:19][CH2:18][CH:17]1[N:26]1[CH2:30][CH2:29][CH2:28][CH2:27]1>>[CH3:14][N:15]([C@@H:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:19][CH2:18][C@H:17]1[N:26]1[CH2:30][CH2:29][CH2:28][CH2:27]1)[C:11](=[O:13])[CH2:10][C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=1

Participants

3

Reactant 2

HCID 4661(4-Nitrophenyl)acetic acidHCID 14476582N-methyl-2-(1-pyrrolidinyl)-1,2,3,4-tetrahydro-1-naphthalene amine

Product 1

HCID 14476592Trans (+/-) N-methyl-4-nitro-N-[2(1-pyrrolidinyl)-1,2,3,4-tetrahydro-1-naphthyl]-benzene acetamideYield 92%

Procedure

Using the procedure of Step C of Example 1, 770 mg of (p-nitrophenyl) acetic acid and 700 mg of the product of Step B of Example 1 were reacted to obtain 1.4 g of crude product which was purified by chromatograph on silica (eluant: methylene chloride 90, methanol 10) to obtain 1.1 g of product which was crystallized from ethyl ether to obtain 480 mg of product. Two crystallizations from isopropanol were effected to obtain 300 mg of the expected product melting at 135° C.

Workup

  1. customwere reacted
  2. customto obtain 1.4 g of crude product which
  3. customwas purified by chromatograph on silica (eluant: methylene chloride 90, methanol 10)

Sources & evidence

ORD record
ord-054d9bd593414ce4853093068cb778b7
Source dataset
uspto-grants-1992_07
Patent number
US05130329

Reaction notes

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