Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1) → (1R,2S)-2-(4-chlorophenyl)-1'-(2-morpholinoethyl)spiro[cyclopropane-1,3'-indolin]-2'-one

HRID 1805323Notes

Reaction equation

HRID 1805323 reaction equation
Cl.Cl[CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1.[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([C@H:18]2[C@@:20]3([C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[NH:22][C:21]3=[O:29])[CH2:19]2)=[CH:14][CH:13]=1>>[Cl:11][C:12]1[CH:13]=[CH:14][C:15]([C@H:18]2[C@@:20]3([C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[N:22]([CH2:3][CH2:4][N:5]4[CH2:10][CH2:9][O:8][CH2:7][CH2:6]4)[C:21]3=[O:29])[CH2:19]2)=[CH:16][CH:17]=1

Participants

3

Reactant 2

HCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)HCID 58305306(1R,2S)-2-(4-chlorophenyl)spiro[cyclopropane-1,3'-indolin]-2'-one

Product 1

HCID 58305300(1R,2S)-2-(4-chlorophenyl)-1'-(2-morpholinoethyl)spiro[cyclopropane-1,3'-indolin]-2'-one

Procedure

The title compound was prepared in analogy to Example 70 starting from 4-(2-chloroethyl)morpholine hydrochloride (commercially available), (1S,2R) and (1R,2S)-2-(4-chlorophenyl)spiro[cyclopropane-1,3′-indolin]-2′-one prepared as in Scheme 1. LC/MS m/e calcd. for C22H23ClN2O2: 382, observed (M+H)+: 383.1 1H NMR (400 MHz, MeOD-d4) δppm 2.21-2.29 (m, 2 H) 3.30 (t, J=8.72 Hz, 1 H) 3.54-3.69 (m, 2 H) 3.97 (br. s., 8 H) 4.21-4.32 (m, 1 H) 4.36-4.48 (m, 1 H) 6.15 (d, J=7.33 Hz, 1 H) 6.83 (t, J=7.20 Hz, 1 H) 7.14-7.21 (m, 1 H) 7.22-7.30 (m, 3 H) 7.31-7.39 (m, 2 H).

Sources & evidence

ORD record
ord-63826604516c4ec182b706ebfd96d5e8
Source dataset
uspto-grants-2013_01
Patent number
US08354443B2

Reaction notes

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