Oxalic Acid → 4-[3-(3-Naphthalen-2-yl-8-aza-bicyclo[3.2.1]oct-2-en-8-yl)-propoxy]-1H-indole

HRID 987584Notes

Reaction equation

HRID 987584 reaction equation
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[CH:8]=[CH:9][NH:10]2.[CH:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17][C:16]=1[C:25]1[CH2:31][CH:30]2[NH:32][CH:27]([CH2:28][CH2:29]2)[CH:26]=1.C(O)(=O)C(O)=O>CCO>[CH:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17][C:16]=1[C:25]1[CH2:26][CH:27]2[N:32]([CH2:2][CH2:3][CH2:4][O:5][C:6]3[CH:14]=[CH:13][CH:12]=[C:11]4[C:7]=3[CH:8]=[CH:9][NH:10]4)[CH:30]([CH2:29][CH2:28]2)[CH:31]=1

Participants

5

Reactant 3

HCID 971Oxalic AcidHCID 116941694-(3-chloropropoxy)-1H-indoleHCID 119560113-(Naphth-2-yl)-8-azabicyclo[3.2.1]oct-2-ene

Product 1

HCID 101796514-[3-(3-Naphthalen-2-yl-8-aza-bicyclo[3.2.1]oct-2-en-8-yl)-propoxy]-1H-indole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The title compound is prepared according to the procedure of Example 2, Step 3, except that 4-(3-chloropropoxy)-1H-indole is used in place of 4-(2-chloro-ethoxy)-1H-indole and 3-naphthalen-2-yl-8-aza-bicyclo[3.2.1]oct-2-ene is used in place of 3-(8-aza-bicyclo[3.2.1]oct-2-en-3-yl)-1H-indole. The corresponding oxalate salt is prepared by treating the title compound with 1 equiv. of oxalic acid in EtOH. Yield: 35% of a white solid. mp: 118-123° C.; MS (ES) m/z: 409.3 (MH)+.

Workup

  1. customThe title compound is prepared
  2. customThe corresponding oxalate salt is prepared

Sources & evidence

ORD record
ord-aa81cff9659948029c1057434d5e249b
Source dataset
uspto-grants-2003_10
Patent number
US06632824B2

Reaction notes

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