Ammonia → HCID 67542288, compound

HRID 2355831Notes

Reaction equation

HRID 2355831 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([C:8](=O)[CH2:9][N:10]2[CH2:14][CH2:13][CH2:12][CH:11]2[C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH2:22][CH2:23][CH2:24][N:25]3[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]3)[CH:16]=2)[CH:5]=[CH:6][CH:7]=1.N>CO.C(Cl)Cl>[I:1][C:2]1[CH:3]=[C:4]([C@H:8]2[C:20]3[C:15](=[CH:16][C:17]([O:21][CH2:22][CH2:23][CH2:24][N:25]4[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]4)=[CH:18][CH:19]=3)[C@@H:11]3[CH2:12][CH2:13][CH2:14][N:10]3[CH2:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 67543167HCID 67543167, compound

Product 1

HCID 67542288HCID 67542288, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

1-(3-Iodo-phenyl)-2-{2-[3-(3-piperidin-1-yl-propoxy)-phenyl]-pyrrolidin-1-yl}-ethanone. Prepared as described in Example 8, Step 1, on a 3.46 mmol scale, to give 1.0 g (54%) of the desired product as an orange semi-solid after chromatography (NH3 in MeOH/CH2Cl2). MS: exact mass calcd for C26H33IN2O2, 532.2; m/z found, 533.4 [M+H]+. 1H NMR (CDCl3): 8.20 (m, 1H), 7.82 (m, 2H), 7.24 (t, J=7.9, 1H), 7.12 (t, J=7.9, 1H), 6.97 (d, J=7.6, 1H), 6.93 (m, 1H), 6.78 (m, 1H), 3.97 (m, 2H), 3.42 (t, J=8.7, 1H), 3.35 (m, 2H), 2.61 (m, 6H), 2.34 (m, 1H), 2.18 (m, 1H), 2.05 (m, 4H), 1.85 (m, 2H), 1.68 (m, 4h), 1.48 (m, 2H).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-eb974471f3fe41548f211bfb77905c11
Source dataset
uspto-grants-2010_07
Patent number
US07754882B2

Reaction notes

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