Benzyl isocyanate → HCID 10294861, compound

HRID 1371402Notes

Reaction equation

HRID 1371402 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][C:16]=1[Cl:17])[CH2:5][N:6]1[CH2:11][CH2:10][O:9][CH:8]([CH2:12][NH2:13])[CH2:7]1.[CH2:18]([N:25]=[C:26]=[O:27])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>ClCCl>[CH2:18]([NH:25][C:26]([NH:13][CH2:12][CH:8]1[O:9][CH2:10][CH2:11][N:6]([CH2:5][C:4]2[CH:14]=[CH:15][C:16]([Cl:17])=[C:2]([Cl:1])[CH:3]=2)[CH2:7]1)=[O:27])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 76639Benzyl isocyanateHCID 10308229[4-(3,4-Dichlorobenzyl)morpholin-2-yl]methylamine

Product 1

HCID 10294861HCID 10294861, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of Intermediate 3 (0.025 g) in dichloromethane (1 ml) was added benzylisocyanate (16.8 pt). The mixture was stirred at 22° C. for 18 h before tris-(2-aminoethyl)amine polystyrene (Argonaut Technologies, 0.04 g @ 3.85 mmol/g) was added. Stirring was continued for a further 72 h before the mixture was poured onto a 1 g solid phase extraction (Isolute SCX sulphonic acid) cartridge. The cartridge was washed with methanol before eluting with 10% 0.880 ammonia solution in methanol. The basic fraction was evaporated in vacuo to give a pale yellow solid. The solid was purified by eluting through a 1 g silica solid phase extraction cartridge (Varian Bondelut) eluting sequentially with dichloromethane, ether, ethyl acetate, acetone, acetonitrile and methanol, to give the title compound as a white solid (0.031 g). LC/MS (System A) Rt 2.22 min, Mass Spectrum m/z 408 [MH+].

Workup

  1. additionwas added
  2. washThe cartridge was washed with methanol
  3. washbefore eluting with 10% 0.880 ammonia solution in methanol
  4. customThe basic fraction was evaporated in vacuo
  5. customto give a pale yellow solid
  6. customThe solid was purified
  7. washby eluting through a 1 g silica solid phase extraction cartridge (Varian Bondelut)
  8. washeluting sequentially with dichloromethane, ether, ethyl acetate, acetone, acetonitrile and methanol

Sources & evidence

ORD record
ord-e6240a7227e04959ba571b2ed1ce73f6
Source dataset
uspto-grants-2007_01
Patent number
US07157457B2

Reaction notes

Loading…