Proton sponge → HCID 20069038, compound

HRID 982130Notes

Reaction equation

HRID 982130 reaction equation
C([N:8]1[CH2:16][C:15]2[C:14]3[CH:17]=[CH:18][CH:19]=[C:20]([O:21][CH3:22])[C:13]=3[CH2:12][CH:11]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:10]=2[CH2:9]1)C1C=CC=CC=1.CN(C)C1C2C(=CC=CC=2N(C)C)C=CC=1.[Cl:45]C(OC(Cl)=O)C>ClCCCl>[ClH:45].[CH3:22][O:21][C:20]1[C:13]2[CH2:12][CH:11]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:10]3[CH2:9][NH:8][CH2:16][C:15]=3[C:14]=2[CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 88675Proton spongeHCID 5213051-Chloroethyl chloroformateHCID 20069034HCID 20069034, compound

Product 1

HCID 20069038HCID 20069038, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 0.89 g (2.52 mmol) of 2-benzyl-6-methoxy-4-phenyl-2,3,4,5-tetrahydrobenzo[e]isoindole, from Step 6, in 22 mL of 1,2-dichloroethane is added 0.11 g (0.05 mmol) of 1,8-bis(dimethylamino)-naphthalene and 0.33 mL (3.15 mmol) of 1-chloroethylchloroformate at 0° C. The solution is heated to reflux for 2 h and the solvent removed in vacuo. The residue is filtered through silica gel, eluting with 25% ethyl acetate in hexanes. After concentration under reduced pressure, methanol (20 mL) is added and the solution is heated to reflux for 30 minutes, before the solvent is removed in vacuo to give the title compound.

Workup

  1. temperatureThe solution is heated
  2. temperatureto reflux for 2 h
  3. customthe solvent removed in vacuo
  4. filtrationThe residue is filtered through silica gel
  5. washeluting with 25% ethyl acetate in hexanes
  6. concentrationAfter concentration under reduced pressure, methanol (20 mL)
  7. additionis added
  8. temperaturethe solution is heated
  9. temperatureto reflux for 30 minutes, before the solvent
  10. customis removed in vacuo

Sources & evidence

ORD record
ord-8ab2e5c612a74c30ae20af96f43614bc
Source dataset
uspto-grants-1991_02
Patent number
US04994486

Reaction notes

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