Indole → 1H-Indole, 7-(1-piperazinyl)-

HRID 1371517Notes

Reaction equation

HRID 1371517 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.BrC1C=CC=C2C=1NC=C2.C([N:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1)(OC(C)(C)C)=O.C(O)(C(F)(F)F)=O>C(Cl)Cl>[N:27]1([C:8]2[CH:7]=[CH:6][CH:5]=[C:4]3[C:9]=2[NH:1][CH:2]=[CH:3]3)[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1

Participants

6

Reactant 4

HCID 798IndoleHCID 6422Trifluoroacetic acidHCID 143452tert-Butyl piperazine-1-carboxylateHCID 27570207-Bromoindole

Product 1

HCID 30695021H-Indole, 7-(1-piperazinyl)-Yield 54%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The Boc protected indole (200 mg, 1.5 mmol) prepared from 7-bromoindole and N-Boc piperazine as described in Step 1 of Preparation 54A is dissolved in DCM (1 mL). TFA (1 mL) is added and the mixture is stirred at r.t. for about an hour. The mixture is then concentrated to oil, which is taken up in methanol and freebased via SCX purification to afford about 164 mg (54%) of the final compound.

Workup

  1. concentrationThe mixture is then concentrated to oil, which
  2. customis taken up in methanol and freebased via SCX purification

Sources & evidence

ORD record
ord-b3442d9115a648a3bce533b88e405f98
Source dataset
uspto-grants-2007_01
Patent number
US07157463B2

Reaction notes

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