1-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)piperidin-4-yl acetate → N,N-dimethyl-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)piperidin-4-amine

HRID 447307Notes

Reaction equation

HRID 447307 reaction equation
C(O[CH:5]1[CH2:10][CH2:9][N:8]([C:11]2[CH:16]=[CH:15][C:14]([B:17]3[O:21][C:20]([CH3:23])([CH3:22])[C:19]([CH3:25])([CH3:24])[O:18]3)=[CH:13][CH:12]=2)[CH2:7][CH2:6]1)(=O)C.BrC1C=C[C:30]([N:33]2CCC(N(C)C)C[CH2:34]2)=CC=1>>[CH3:30][N:33]([CH3:34])[CH:5]1[CH2:10][CH2:9][N:8]([C:11]2[CH:16]=[CH:15][C:14]([B:17]3[O:21][C:20]([CH3:23])([CH3:22])[C:19]([CH3:25])([CH3:24])[O:18]3)=[CH:13][CH:12]=2)[CH2:7][CH2:6]1

Participants

3

Reactant 2

HCID 667303481-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)piperidin-4-yl acetateHCID 667303771-(4-bromophenyl)-N,N-dimethylpiperidin-4-amine

Product 1

HCID 58486272N,N-dimethyl-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)piperidin-4-amineYield 23%

Conditions

Temperature
120 °C

Procedure

The title compound was synthesized according to the method described for the synthesis of 1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)piperidin-4-yl acetate, except substituting 1-(4-bromophenyl)-N,N-dimethylpiperidin-4-amine (139 mg, 0.49 mmol) and the reaction was heated to 120° C. for 4 h. Crude product was purified by flash chromatography using EtOAc/Et3N as eluent (1:0 to 98:2) to give the title compound as a yellow solid (37 mg, 23%). 1H NMR (400 MHz, MeOD) δ 7.61 (d, J=8.6 Hz, 2H), 6.92 (d, J=8.5 Hz, 2H), 3.89-3.86 (m, 2H), 2.75-2.69 (m, 2H), 2.36-2.30 (m, 1H), 2.30 (s, 6H), 1.96-1.64 (m, 2H), 1.65-1.48 (m, 2H), 1.32 (s, 12H); MS ESI 331.1 [M+H]+, calcd for [C19H31BN2O2+H]+ 331.25.

Workup

  1. customThe title compound was synthesized
  2. customCrude product was purified by flash chromatography

Sources & evidence

ORD record
ord-57df1c49408a4c6dba73b6d27a44df9e
Source dataset
uspto-grants-2013_07
Patent number
US08481533B2

Reaction notes

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