4-Piperidinecarboxamide → 1-(3-Methoxyphenyl)piperidine-4-carboxamide
Reaction equation
COc1cccc(Br)c1.NC(=O)C1CCNCC1>CC(=O)O.CC(=O)O.CC(C)CN1CCN2CCN(CC(C)C)P1N(CC(C)C)CC2.C[Si](C)(C)[N-][Si](C)(C)C.Cc1ccccc1.[Li+].[Pd]>COc1cccc(N2CCC(C(N)=O)CC2)c1Participants
7
Conditions
- Temperature
- 100 °C
Procedure
piperidine-4-carboxamide (0.411 g, 3.21 mmol); 1-bromo-3-methoxybenzene (0.339 mL, 2.67 mmol) and diacetoxypalladium (0.120 g, 0.53 mmol) were thoroughly placed under an inert atmoshere. To this was added 2,8,9-triisobutyl-2,5,8,9-tetraaza-1-phosphabicyclo[3.3.3]undecane (0.037 g, 0.11 mmol); LITHIUM BIS(TRIMETHYLSILYL)AMIDE (6.15 mL, 6.15 mmol) and toluene (10 mL). The resultant mixture was stirred at 100 °C overnight. No sign of reaction by LCMS overnight. Abandoned
Sources & evidence
- ORD record
- ord-c91f5415f0604adda8f4b73dd97ab0f8
- Source dataset
- 750 AstraZeneca ELN dataset
- Original link
- View source
Reaction notes
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