Tetrahydrofuran → Tert-butyl 4-{3-[(6-bromohexanoyl)amino]phenyl}-1-piperidine carboxylate

HRID 1452650Notes

Reaction equation

HRID 1452650 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([NH2:20])[CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Br:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][C:27](Cl)=[O:28].C(N(CC)CC)C.C1COCC1>C(Cl)(Cl)Cl>[Br:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][C:27]([NH:20][C:16]1[CH:15]=[C:14]([CH:11]2[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:9][CH2:10]2)[CH:19]=[CH:18][CH:17]=1)=[O:28]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 898486-Bromohexanoyl chlorideHCID 22049268tert-Butyl 4-(3-aminophenyl)piperidine-1-carboxylate

Product 1

HCID 57526937Tert-butyl 4-{3-[(6-bromohexanoyl)amino]phenyl}-1-piperidine carboxylateYield 101.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A 25-mL RB-flask, charged with tert-butyl-4-[3-(amino)phenyl]-1-piperidinecarboxylate (2.00 mmol, 0.553 g), 6-bromohexanoyl chloride (0.427 g, 2.00 mmol, 1.0 eq.), triethylamine (0.404 g, 4.00 mmol) and THF (8.00 mL) was stirred at room temperature for 4 h. The reaction mixture was diluted with chloroform (50 mL) and washed with water (100 mL), brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by chromatography (silica gel, hexanes/EtOAc 10:1) to yield the desired product (0.921 g, 95.8%). 1H NMR (400 MHz, CDCl3) δ 7.47 (s, 1H), 7.28-7.22 (m, 2H), 7.11 (s, 1H), 6.5 (d, 1H, J=7.0 Hz), 3.45-3.39 (m, 2H), 2.85-2.70 (m, 2H), 2.68-2.58 (m, 1H), 2.37 (t, 2H, J=7.4 Hz), 1.96-1.71 (m, 7H), 1.68-1.50 (m, 5H), 1.48 (s, 9H); ESMS m/e: 355.4, 476.6.

Workup

  1. washwashed with water (100 mL), brine
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by chromatography (silica gel, hexanes/EtOAc 10:1)

Sources & evidence

ORD record
ord-b3bc0ef9ae9949bc8ca099c773ff4e79
Source dataset
uspto-grants-2009_01
Patent number
US07473698B2

Reaction notes

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