1-Chloromethylnaphthalene → N-(4-Chlorophenyl)-N'-{[4-(1 naphthylmethyl)morpholin-2-yl]methyl}urea

HRID 1371419Notes

Reaction equation

HRID 1371419 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:11][CH2:12][CH:13]2[O:18][CH2:17][CH2:16][NH:15][CH2:14]2)=[O:10])=[CH:4][CH:3]=1.Cl[CH2:20][C:21]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=[CH:23][CH:22]=1>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:11][CH2:12][CH:13]2[O:18][CH2:17][CH2:16][N:15]([CH2:20][C:21]3[C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[CH:24]=[CH:23][CH:22]=3)[CH2:14]2)=[O:10])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 68451-ChloromethylnaphthaleneHCID 23089254N-(4-Chlorophenyl)-N'-(morpholin-2-ylmethyl)urea

Product 1

HCID 17984726N-(4-Chlorophenyl)-N'-{[4-(1 naphthylmethyl)morpholin-2-yl]methyl}urea

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of Intermediate 9 (0.01 g) in N,N-dimethylformamide (1 ml) was added 1-(chloromethyl)naphthalene (6.1 μl). The mixture was stirred at 22° C. for 24 h before tris-(2-aminoethyl)amine polystyrene (Argonaut Technologies, 0.01 g @ 4.46 mmol/g) and polystyrene methyl isocyanate (Argonaut Technologies, 0.033 g @ 1.39 mmol/g) was added. Stirring was continued for a further 2 h before the mixture was purified by solid phase extraction (Isolute SCX sulphonic acid column), eluting with methanol followed by 10% 0.880 ammonia solution in methanol. The basic fraction was evaporated in vacuo to give the title compound (0.003 g). LC/MS (System A) Rt 2.82 min, Mass Spectrum m/z 4140 [MH+].

Workup

  1. additionwas added
  2. customwas purified by solid phase extraction (Isolute SCX sulphonic acid column)
  3. washeluting with methanol
  4. customThe basic fraction was evaporated in vacuo

Sources & evidence

ORD record
ord-4972870b008c4989915a16eccce2a1f7
Source dataset
uspto-grants-2007_01
Patent number
US07157457B2

Reaction notes

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