Acetyl chloride → 4-[(Trimethylsilyl)ethynyl]-1,2,3,6-tetrahydropyridine hydrochloride

HRID 1992322Notes

Reaction equation

HRID 1992322 reaction equation
[CH3:1][Si:2]([C:5]#[C:6][C:7]1[CH2:8][CH2:9][N:10](C(OC(C)(C)C)=O)[CH2:11][CH:12]=1)([CH3:4])[CH3:3].C([Cl:23])(=O)C.CCOC(C)=O>CO>[ClH:23].[CH3:1][Si:2]([C:5]#[C:6][C:7]1[CH2:12][CH2:11][NH:10][CH2:9][CH:8]=1)([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8857Ethyl AcetateHCID 18942192tert-Butyl 4-[(trimethylsilyl)ethynyl]-3,6-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 673510094-[(Trimethylsilyl)ethynyl]-1,2,3,6-tetrahydropyridine hydrochlorideYield 75.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

tert-Butyl 4-[(trimethylsilyl)ethynyl]-3,6-dihydropyridine-1(2H)-carboxylate (2.75 g, 9.8 mmol) was stirred in methanol (10 mL) and acetyl chloride (2.1 mL, 29.2 mmol) was added dropwise. The temperature rose from 18° C. to 30° C. during the addition, and the mixture was kept at 40° C. until there was no more starting material by tlc. The mixture was cooled to room temperature, EtOAc (15 mL) was added and the solid filtered off to give an off-white solid (1.6 g).

Workup

  1. additionThe temperature rose from 18° C. to 30° C. during the addition
  2. customwas kept at 40° C. until there
  3. filtrationthe solid filtered off

Sources & evidence

ORD record
ord-1638221abe5a43ac9fea235a5edc6b80
Source dataset
uspto-grants-2010_01
Patent number
US07648992B2

Reaction notes

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