Sodium hydride → 1-(3-{4-[1-(3-Piperidin-1-yl-propyl)-1H-pyrrol-2-yl]-phenoxy}-propyl)-piperidine

HRID 33732

Reaction equation

HRID 33732 reaction equation
[H-].[Na+].[NH:3]1[CH:7]=[CH:6][CH:5]=[C:4]1[C:8]1[CH:23]=[CH:22][C:11]([O:12][CH2:13][CH2:14][CH2:15][N:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)=[CH:10][CH:9]=1.Cl[CH2:25][CH2:26][CH2:27][N:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1>CN(C=O)C.O>[N:28]1([CH2:27][CH2:26][CH2:25][N:3]2[CH:7]=[CH:6][CH:5]=[C:4]2[C:8]2[CH:23]=[CH:22][C:11]([O:12][CH2:13][CH2:14][CH2:15][N:16]3[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)=[CH:10][CH:9]=2)[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 79625Piperidine, 1-(3-chloropropyl)-HCID 179626131-{3-[4-(1H-Pyrrol-2-yl)-phenoxy]-propyl}-piperidine

Product 1

HCID 102949771-(3-{4-[1-(3-Piperidin-1-yl-propyl)-1H-pyrrol-2-yl]-phenoxy}-propyl)-piperidineYield 89.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a stirred suspension of sodium hydride (0.051 g) in DMF (3 mL) at RT was added dropwise the product of Example 18 (0.2 g) in DMF (4 mL). After 20 min, 1-(3-chloro-propyl)-piperdine (0.139 g) was added dropwise and the mixture stirred for 12 h. The mixture was diluted with water and extracted several times with diethyl ether. The combined organic layers were washed with brine, dried (sodium sulfate), filtered and concentrated under reduced pressure, giving the title compound as a dark red oil (0.257 g). 1H NMR (400 MHz, C6D6): 7.35 (d, J=8.8 Hz, 2H), 6.90 (d, J=8.8 Hz, 2H), 6.72 (t, J=2.5 Hz, 1H), 6.44 (d, J=2.5 Hz), 3.82 (m, 4H), 2.37-2.16 (m, 8H), 2.06 (br s, 4H), 1.96 (t, J=6.6 Hz, 2H), 1.87-1.81 (m, 2H), 1.59-1.22 (m, 16H).

Workup

  1. extractionextracted several times with diethyl ether
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried (sodium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-cc46cb2230db48b88db4dd9f640a6651
Source dataset
uspto-grants-2008_09
Patent number
US07429586B2

Linked notes

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