Reaction #48121

ord-c022ecaf67d6430282e88dea5a80a881

Reaction equation

CC(C)N1CCC(Oc2ccc3[nH]c(C(=O)N4CCOCC4)cc3c2)CC1
[5-(1-isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]-morpholin-4-yl-methanone
CC(C)N1CCC(Oc2ccc3[nH]c(C(=O)N4CCOCC4)cc3c2)CC1
intermediate 2
CC(C)N1CCC(Oc2ccc3[nH]c(C(=O)N4CCOCC4)cc3c2)CC1
[5-(1-isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]-morpholin-4-yl-methanone
BrCc1ccccc1
benzyl bromide
→
CC(C)N1CCC(Oc2ccc3c(c2)cc(C(=O)N2CCOCC2)n3Cc2ccccc2)CC1
title compound
CC(C)N1CCC(Oc2ccc3c(c2)cc(C(=O)N2CCOCC2)n3Cc2ccccc2)CC1
[1-Benzyl-5-(1-isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]-morpholin-4-yl-methanone

Reactants

CC(C)N1CCC(Oc2ccc3[nH]c(C(=O)N4CCOCC4)cc3c2)CC1
[5-(1-isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]-morpholin-4-yl-methanone
CC(C)N1CCC(Oc2ccc3[nH]c(C(=O)N4CCOCC4)cc3c2)CC1
intermediate 2
CC(C)N1CCC(Oc2ccc3[nH]c(C(=O)N4CCOCC4)cc3c2)CC1
[5-(1-isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]-morpholin-4-yl-methanone
BrCc1ccccc1
benzyl bromide

Reagents

None

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherIn analogy to the procedure described for the synthesis of example 1

Procedure

In analogy to the procedure described for the synthesis of example 1, the title compound was synthesized from [5-(1-isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]-morpholin-4-yl-methanone (intermediate 2) and benzyl bromide. The title compound was obtained in 4% yield as white solid. MS (m/e): 462.2 (MH+, 100%).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07745479B2uspto-grants-2010_06