Sodium Iodide → 8-[3-(Diphenylamino)propyl]-1-(4-methoxyphenyl)-1,3,8-triazaspiro[4,5]decan-4-one

HRID 648353Notes

Reaction equation

HRID 648353 reaction equation
[C:1]1([N:7]([CH2:14][CH2:15][CH2:16]Br)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([N:26]2[C:30]3([CH2:35][CH2:34][NH:33][CH2:32][CH2:31]3)[C:29](=[O:36])[NH:28][CH2:27]2)=[CH:22][CH:21]=1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[Na+]>C(C(C)=O)C>[C:1]1([N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:14][CH2:15][CH2:16][N:33]2[CH2:34][CH2:35][C:30]3([N:26]([C:23]4[CH:22]=[CH:21][C:20]([O:19][CH3:18])=[CH:25][CH:24]=4)[CH2:27][NH:28][C:29]3=[O:36])[CH2:31][CH2:32]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 108273293-[N,N-diphenylamino)-1-bromopropaneHCID 132402171-(4-Methoxyphenyl)-1,3,8-triazaspiro[4.5]decan-4-one3×

Product 1

HCID 127638658-[3-(Diphenylamino)propyl]-1-(4-methoxyphenyl)-1,3,8-triazaspiro[4,5]decan-4-one

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 940 mg. (0.00325 moles) of 3-[N,N-diphenylamino]-1-bromopropane (prepared according to the procedure of Example 2) and 850 mg. (0.00325 moles) of 1-(4-methoxyphenyl)-1,3,8-triazaspiro[4,5]decan-4-one, 400 mg. of sodium carbonate and 100 mg. of sodium iodide in 15 ml. of methyl ethyl ketone is refluxed for about 16 hours. The preparation of 1-(4-methoxyphenyl)-1,3,8-triazaspiro[4,5]decan-4-one is described in U.S. Pat. No. 3,155,670 to Janssen, issued Nov. 3, 1964. Solvent is evaporated and the residue is dissolved in chloroform, washed with water and chromatographed on a column of silica gel. The product fractions are evaporated and the residue is recrystallized from isopropyl alcohol and again from ethanol, giving 470 mg. of 8-[3-diphenylamino)propyl]-1-(4-methoxyphenyl)-1,3,8-triazaspiro[4,5]decan-4-one, mp. 156.5°-157.5° C.

Workup

  1. additionA mixture of 940 mg
  2. customSolvent is evaporated
  3. dissolutionthe residue is dissolved in chloroform
  4. washwashed with water
  5. customchromatographed on a column of silica gel
  6. customThe product fractions are evaporated
  7. customthe residue is recrystallized from isopropyl alcohol and again from ethanol
  8. customgiving 470 mg

Sources & evidence

ORD record
ord-931ee8ff182f42cb9a930b209982cbaa
Source dataset
uspto-grants-1983_10
Patent number
US04411904

Reaction notes

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