Triethylamine → HCID 67492747, compound

HRID 1922381Notes

Reaction equation

HRID 1922381 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:4][CH2:3]1.CCN(CC)CC.[Br:22][CH:23]([CH3:27])[C:24](Br)=[O:25]>C(Cl)Cl.O>[Br:22][CH:23]([CH3:27])[C:24]([N:8]([CH:5]1[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:25]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 79047Propanoyl bromide, 2-bromo-HCID 896421-Methyl-N-phenylpiperidin-4-amine

Product 1

HCID 67492747HCID 67492747, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of compound 1-methyl-N-phenylpiperidin-4-amine (1.0 g, 5.255 mmol) in dry CH2Cl2 (10 mL) was treated with Et3N (2.19 mL, 15.766 mmol) followed by 2-bromopropionyl bromide (0.61 mL, 5.780 mmol) at 0° C. and stirred at same temperature for 1 h. The reaction was diluted with water (25 mL) and product was extracted into CH2Cl2 (2×25 mL). The combined CH2Cl2 layer was washed with brine (20 mL) and dried (Na2SO4). Solvent was evaporated and crude was purified by column chromatography (MeOH:CH2Cl2, 5:95) to obtain compound 2-Bromo-N-(1-methylpiperidin-4-yl)-N-phenylpropanamide (1.5 g, 88%) as a solid. 1H NMR (DMSO-d6) δ: 1.09-1.33 (m, 2H), 1.59 (d, 3H, J=6.3 Hz), 1.66-1.74 (m, 2H), 1.89-1.98 (m, 2H), 2.09 (s, 3H), 2.68-2.74 (m, 2H), 4.01 (q, 1H), 4.28-4.36 (m, 1H), 7.26-7.30 (m, 2H), 7.46-7.50 (m, 3H); ESI-MS (m/z, %) 327 and 325 (MH+, 100%).

Workup

  1. extractionwas extracted into CH2Cl2 (2×25 mL)
  2. washThe combined CH2Cl2 layer was washed with brine (20 mL)
  3. dry with materialdried (Na2SO4)
  4. customSolvent was evaporated
  5. customcrude was purified by column chromatography (MeOH:CH2Cl2, 5:95)

Sources & evidence

ORD record
ord-2186d1b6abd8433996b506b888a04247
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

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