Chlorotrimethylsilane → Methyl 4-(piperidin-4-yl)butanoate

HRID 1097288Notes

Reaction equation

HRID 1097288 reaction equation
[CH3:1][Si](Cl)(C)C.[NH:6]1[CH2:11][CH2:10][CH:9]([CH2:12][CH2:13][CH2:14][C:15]([OH:17])=[O:16])[CH2:8][CH2:7]1>CO>[CH3:1][O:16][C:15](=[O:17])[CH2:14][CH2:13][CH2:12][CH:9]1[CH2:10][CH2:11][NH:6][CH2:7][CH2:8]1

Participants

4

Reactant 2

HCID 6397ChlorotrimethylsilaneHCID 51677024-(Piperidin-4-yl)butanoic acid

Product 1

HCID 21462751Methyl 4-(piperidin-4-yl)butanoateYield 100.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Trimethylsilyl chloride (9.2 ml, 72.46 mmol) was added to a solution of 4-piperidin-4-yl-butyric acid (1) (5.00 g, 24.15 mmol) dissolved in anhydrous methanol (100 mL). The resulting solution was stirred at room temperature for 48 hours, and concentrated under vacuum to complete dryness to give 2 (4.50 g, 97%) as a white solid, which was used directly in the next step without further purification: 1H NMR (300 MHz, CD3OD) δ 1.20-1.46 (m, 4H), 1.52-1.74 (m, 3H), 1.96 (d, 2H), 2.35 (t, 2H), 2.96 (t, 2H), 3.36 (t, 2H), 3.68 (s, 3H); ESI MS m/z 186 [C10H19NO2+H]+.

Workup

  1. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-5852ea171c3842fe9dcd0c6d841c6200
Source dataset
uspto-grants-2012_03
Patent number
US08143256B2

Reaction notes

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