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

HRID 1902669Notes

Reaction equation

HRID 1902669 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 United States 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-ca2dfeacb2ab464aab1eef43514fba43
Source dataset
uspto-grants-1982_12
Patent number
US04364954

Reaction notes

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