5-Isocyanato-1,2,3-trimethoxybenzene → HCID 22022836, compound

HRID 1793646Notes

Reaction equation

HRID 1793646 reaction equation
ClC1C=CC(CC2CC3N(CC(N)C)C(CC3)C2)=CC=1.C[O:22][C:23]1[CH:24]=[C:25]([N:33]=[C:34]=[O:35])[CH:26]=[C:27](OC)[C:28]=1OC>C(Cl)Cl>[OH:22][CH:23]1[CH2:24][CH:25]2[CH2:26][CH2:27][CH:28]1[C:34](=[O:35])[NH:33]2

Participants

4

Reactant 2

HCID 5177665-Isocyanato-1,2,3-trimethoxybenzeneHCID 22022835HCID 22022835, compound

Product 1

HCID 22022836HCID 22022836, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-[3-(4-chlorobenzyl)-8-aza-bicyclo[3.2.1]oct-8-yl]-1-methyl-ethylamine in CH2Cl2 was added 3,4,5-trimethoxyphenylisocyanate at −78° C. After the addition, it was allowed to warm up to rt where it was stirred for 4 h. It was then diluted with CH2Cl2. The organic layer was washed with NaCl (sat.) and dried over Na2SO4. The crude product was purified on a silica-gel column with 3% (10% iPr-NH2 in MeOH) in EtOAc to give 55% of Example 4 (m.p. 115–120° C., M+: 502).

Workup

  1. additionAfter the addition, it
  2. washThe organic layer was washed with NaCl (sat.)
  3. dry with materialdried over Na2SO4
  4. customThe crude product was purified on a silica-gel column with 3% (10% iPr-NH2 in MeOH) in EtOAc

Sources & evidence

ORD record
ord-a4d774f7c7a4402abeb9dbcc1620b356
Source dataset
uspto-grants-2006_07
Patent number
US07081531B2

Reaction notes

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