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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1805383Generated: November 3, 2026

1,2-Dibromoethene → (1R,2S)-2-(4-chlorophenyl)-1'-(2-(3-morpholinopropylamino)ethyl) spiro[cyclopropane-1,3'-indolin]-2'-one

https://huagongshe.com/reaction/1805383

Reaction equation

Participants

RoleNameHCIDCharge
Reactant1,2-DibromoetheneHCID 10897—
ReactantN-(3-Aminopropyl)morpholineHCID 61055—
Reactant(1S,2R)-2-(4-chlorophenyl)spiro[cyclopropane-1,3'-indolin]-2'-oneHCID 58305285—
Product(1R,2S)-2-(4-chlorophenyl)-1'-(2-(3-morpholinopropylamino)ethyl) spiro[cyclopropane-1,3'-indolin]-2'-oneHCID 58305419—

Reaction Steps

The title compound was prepared in analogy to Example 81 starting from dibromo ethylene, 3-morpholinopropan-1-amine (commercially available), (1R,2S) and (1S,2R)-2-(4-chlorophenyl)spiro[cyclopropane-1,3′-indolin]-2′-one prepared as in Scheme 1. LC/MS m/e calcd. for C25H30ClN3O2: 439, observed (M+H)+: 440.1 1HNMR (400 MHz, MeOD-d4) δppm 2.07-2.32 (m, 6 H) 3.26 (s, 8 H) 3.47 (t, J=5.94 Hz, 3 H) 4.24 (d, J=28.55 Hz, 3 H) 6.12 (d, J=7.07 Hz, 1 H) 6.81 (t, J=7.07 Hz, 1 H) 7.14 (d, J=7.58 Hz, 1 H) 7.19-7.29 (m, 3H) 7.30-7.39 (m, 2 H).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08354443B2
Source datasetuspto-grants-2013_01
ORD IDord-c9d4d1205c7044df996fddfbb4391077
Source noteuspto-grants-2013_01