4-Methoxyphenyl isothiocyanate → N-[[1-[(2,3-dihydro-1,4-benzodioxin-2-yl)methyl]-4-piperidinyl]methyl]-N'-(4-methoxyphenyl)thiourea

HRID 579803Notes

Reaction equation

HRID 579803 reaction equation
Br.Br.[O:3]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[O:6][CH2:5][CH:4]1[CH2:13][N:14]1[CH2:19][CH2:18][CH:17]([CH2:20][NH2:21])[CH2:16][CH2:15]1.[O-2].[Ca+2].[N:24]([C:27]1[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=1)=[C:25]=[S:26]>CO>[O:3]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[O:6][CH2:5][CH:4]1[CH2:13][N:14]1[CH2:15][CH2:16][CH:17]([CH2:20][NH:21][C:25]([NH:24][C:27]2[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=2)=[S:26])[CH2:18][CH2:19]1

Participants

5

Reactant 3

HCID 752934-Methoxyphenyl isothiocyanateHCID 6850728CalciumoxideHCID 140490391-[(2,3-Dihydro-1,4-benzodioxin-2-yl)methyl]-4-piperidinemethanamine dihydrobromide

Product 1

HCID 14049040N-[[1-[(2,3-dihydro-1,4-benzodioxin-2-yl)methyl]-4-piperidinyl]methyl]-N'-(4-methoxyphenyl)thiourea

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 6.4 parts of (1-[(2,3-dihydro-1,4-benzodioxin-2-yl)methyl]-4-piperidinemethanamine dihydrobromide, 4 parts of calcium oxide and 80 parts of methanol was stirred for 3 hours at room temperature. Then there were added 5 parts of 1-isothiocyanato-4-methoxybenzene and the whole was stirred for 3 hours at room temperature. The whole was filtered and the filtrate was evaporated. The sticky residue was suspended in a mixture of 1,1'-oxybisethane and 2,2'-oxybispropane, the latter was decanted (the residue was set aside) and allowed to crystallize, yielding a first fraction of 1 part of N-[[1-[(2,3-dihydro-1,4-benzodioxin-2-yl)methyl]-4-piperidinyl]methyl]-N'-(4-methoxyphenyl)thiourea (intermediate 91). The residue, which was set aside, yield a second fraction of 5 parts of N-[[1-[(2,3-dihydro-1,4-benzodioxin-2-yl)methyl]-4-piperidinyl]methyl]-N'-(4-methoxyphenyl)thiourea (intermediate 91).

Workup

  1. stirringthe whole was stirred for 3 hours at room temperature
  2. filtrationThe whole was filtered
  3. customthe filtrate was evaporated
  4. additionThe sticky residue was suspended in a mixture of 1,1'-oxybisethane and 2,2'-oxybispropane
  5. customthe latter was decanted (the residue
  6. customto crystallize

Sources & evidence

ORD record
ord-c87ffe0aef374d38a207630129898cc0
Source dataset
uspto-grants-1988_06
Patent number
US04749702

Reaction notes

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