Triethylamine → HCID 24850733, compound

HRID 2365931Notes

Reaction equation

HRID 2365931 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH:12]1[CH2:17][CH2:16][N:15]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)[CH2:14][CH2:13]1)[C:5](O)=[O:6].C(N(CC)CC)C.O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[CH2:57]([N:64]1[CH2:69][CH2:68][CH:67]([NH2:70])[CH2:66][CH2:65]1)[C:58]1[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1>CN(C)C=O>[CH2:57]([N:64]1[CH2:69][CH2:68][CH:67]([NH:70][C:5](=[O:6])[C:4]2[CH:8]=[CH:9][C:10]([O:11][CH:12]3[CH2:13][CH2:14][N:15]([CH2:18][C:19]4[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=4)[CH2:16][CH2:17]3)=[C:2]([Cl:1])[CH:3]=2)[CH2:66][CH2:65]1)[C:58]1[CH:59]=[CH:60][CH:61]=[CH:62][CH:63]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 4158521-Benzyl-4-piperidylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 67389873HCID 67389873, compound

Product 1

HCID 24850733HCID 24850733, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred mixture of 3-chloro-4-(1-(4-methoxybenzyl)piperidin-4-yloxy)benzoic acid in anhydrous dimethylformamide (0.5 mL) was added triethylamine (0.03 g, 0.30 mmol), 1-hydroxybenzotriazole hydrate (0.02 g, 0.15 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.03 g, 0.15 mmol) and 1-benzylpiperidin-4-amine (0.03 mg, 0.15 mmol). The mixture was stirred at room temperature overnight and then concentrated under reduced pressure. The residue obtained was purified by flash chromatography (silica gel, methylene chloride/methanol/30% ammonium hydroxide=15/1/0.05) to afford N-(1-benzylpiperidin-4-yl)-3-chloro-4-(1-(4-methoxybenzyl)-piperidin-4-yloxy)-benzamide as a white solid (0.01 g, 18%). 1H-NMR (CDCl3, 300 MHz): δ 7.76 (m, 1H), 7.60 (m, 1H), 7.30 (m, 7H), 6.94 (m, 1H), 6.87 (m, 2H), 5.83 (d, J=7.2 Hz, 1H), 4.52 (m, 1H), 3.97 (m, 1H), 3.80 (s, 3H), 3.54 (s, 4H), 2.86 (m, 4H), 2.11 (m, 8H), 1.58 (m, 4H); LCMS: >98%; MS (ESI): 548.2 (M+1), 546.2 (M−1).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue obtained
  3. customwas purified by flash chromatography (silica gel, methylene chloride/methanol/30% ammonium hydroxide=15/1/0.05)

Sources & evidence

ORD record
ord-52aaaac7a16b40de85979dfc6a3ea2dd
Source dataset
uspto-grants-2014_04
Patent number
US08697727B2

Reaction notes

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