1-Chloro-2-(diethylamine)ethane hydrochloride → (1R,2S)-2-(4-chlorophenyl)-1'-(2-(diethylamino)ethyl)spiro[cyclopropane-1,3'-indolin]-2'-one

HRID 1805322Notes

Reaction equation

HRID 1805322 reaction equation
Cl.Cl[CH2:3][CH2:4][N:5]([CH2:8][CH3:9])[CH2:6][CH3:7].[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([C@H:17]2[C@@:19]3([C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[NH:21][C:20]3=[O:28])[CH2:18]2)=[CH:13][CH:12]=1>>[Cl:10][C:11]1[CH:12]=[CH:13][C:14]([C@H:17]2[C@@:19]3([C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[N:21]([CH2:3][CH2:4][N:5]([CH2:8][CH3:9])[CH2:6][CH3:7])[C:20]3=[O:28])[CH2:18]2)=[CH:15][CH:16]=1

Participants

3

Reactant 2

HCID 133631-Chloro-2-(diethylamine)ethane hydrochlorideHCID 58305306(1R,2S)-2-(4-chlorophenyl)spiro[cyclopropane-1,3'-indolin]-2'-one

Product 1

HCID 58305330(1R,2S)-2-(4-chlorophenyl)-1'-(2-(diethylamino)ethyl)spiro[cyclopropane-1,3'-indolin]-2'-one

Procedure

The title compound was prepared in analogy to Example 70 starting from 2-Chloro-N,N-diethylethaneamine 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 C22H25ClN20: 368, observed (M+H)+: 369.1 1H NMR (400 MHz, MeOD-d4) δppm 1.41 (t, J=7.20 Hz, 6 H) 2.21-2.31 (m, 2 H) 3.32 (t, J=8.59 Hz, 1 H) 3.39-3.55 (m, 4 H) 3.60 (t, J=6.44 Hz, 2 H) 4.23-4.42 (m, 2 H) 6.16 (d, J=7.58 Hz, 1 H) 6.85 (t, J=7.45 Hz, 1 H) 7.19 (d, J=7.83 Hz, 1 H) 7.24-7.32 (m, 3 H) 7.33-7.40 (m, 2 H).

Sources & evidence

ORD record
ord-999a2ad6358141c791bb454aa53283f1
Source dataset
uspto-grants-2013_01
Patent number
US08354443B2

Reaction notes

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