1-Bromooctane → HCID 21906868, compound

HRID 1246944Notes

Reaction equation

HRID 1246944 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][CH:13]=[CH:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC([O-])(C)C.[K+].Br[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32]>C1COCC1>[CH2:25]([N:14]1[C:15]2[C:11](=[CH:10][C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[CH:17][CH:16]=2)[CH:12]=[CH:13]1)[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32]

Participants

5

Reactant 3

HCID 81401-BromooctaneHCID 146245-BenzyloxyindoleHCID 23665647Potassium tert-butoxide

Product 1

HCID 21906868HCID 21906868, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

N-Octyl-5-benzyloxyindole was prepared by general method A. 5-Benzyloxyindole (500 mg, 2.24 mmol) was dissolved in THF (20 mL) and treated with 1M KOtBu in THF (3.81 mL, 3.8 mmol). After stirring for 3 hours, 1-bromooctane (0.39 mL, 2.24 mmol) was added and the reaction mixture was stirred for an additional 24 hrs. Standard aqueous workup and purification by silica gel chromatography, eluting with 3:1 hexane/ethyl acetate, provided N-octyl-5-benzyloxyindole. 1H NMR (200 MHz, CDCl3) δ 7.68 (m, 7H), 7.35 (m, 2H), 6.78 (d, J=2.9 Hz, 1H), 5.40 (s, 2H), 4.23 (t, J=7.0 Hz, 2H), 2.05 (broad t, J=6.5 Hz, 2H), 1.62 (broad s, 10H), 1.31 (t, J=6.2 Hz, 3H)

Workup

  1. customN-Octyl-5-benzyloxyindole was prepared by general method A
  2. stirringthe reaction mixture was stirred for an additional 24 hrs
  3. customStandard aqueous workup and purification by silica gel chromatography
  4. washeluting with 3:1 hexane/ethyl acetate

Sources & evidence

ORD record
ord-322a6b82d61a43c9820e37f20b532673
Source dataset
uspto-grants-2006_10
Patent number
US07129250B2

Reaction notes

Loading…