4-(Chloromethyl)piperidine → (1R,2S)-2-(4-chlorophenyl)-1'-(piperidin-4-ylmethyl) Spiro[cyclopropane-1,3'-indolin]-2'-one

HRID 1805381Notes

Reaction equation

HRID 1805381 reaction equation
Cl[CH2:2][CH:3]1[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1.[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([C@@H:16]2[C@:18]3([C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[NH:20][C:19]3=[O:27])[CH2:17]2)=[CH:12][CH:11]=1>>[Cl:9][C:10]1[CH:11]=[CH:12][C:13]([C@H:16]2[C@@:18]3([C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[N:20]([CH2:2][CH:3]4[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]4)[C:19]3=[O:27])[CH2:17]2)=[CH:14][CH:15]=1

Participants

3

Reactant 2

HCID 4292384-(Chloromethyl)piperidineHCID 58305285(1S,2R)-2-(4-chlorophenyl)spiro[cyclopropane-1,3'-indolin]-2'-one

Product 1

HCID 58305342(1R,2S)-2-(4-chlorophenyl)-1'-(piperidin-4-ylmethyl) Spiro[cyclopropane-1,3'-indolin]-2'-one

Procedure

The title compound was prepared in analogy to Example 70 starting from 4-(chloromethyl)piperidine (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 C22H23ClN2O: 366, observed (M+H)+: 367.2 1HNMR (400 MHz, MeOD-d4) δppm 1.51-1.67 (m, 2 H) 1.96 (br. s., 2 H) 2.12-2.21 (m, 2 H) 2.21-2.35 (m, 1 H) 2.93-3.07 (m, 2 H) 3.22 (t, J=8.59 Hz, 1 H) 3.38-3.50 (m, 2 H) 3.84 (d, J=7.33 Hz, 2 H) 6.09 (d, J=7.58 Hz, 1 H) 6.77 (t, J=7.58 Hz, 1 H) 7.11 (d, J=7.83 Hz, 1 H) 7.16-7.26 (m, 3 H) 7.29-7.35 (m, 2 H).

Sources & evidence

ORD record
ord-4d9f2e6616d34bacb0052cc6bdc4745c
Source dataset
uspto-grants-2013_01
Patent number
US08354443B2

Reaction notes

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