4-Phenylpiperidinium chloride → HCID 18348553, compound

HRID 2268536Notes

Reaction equation

HRID 2268536 reaction equation
[CH3:1][O:2][C:3]1[C:4](=[O:29])[C:5]2[CH2:6][CH:7]([CH2:15][CH2:16][CH2:17][CH2:18][O:19][C:20]3[CH:28]=[CH:27][C:23]([C:24](O)=[O:25])=[CH:22][CH:21]=3)[CH2:8][C:9]=2[C:10](=[O:14])[C:11]=1[O:12][CH3:13].Cl.[C:31]1([CH:37]2[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]2)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.Cl.C(N=C=NCCCN(C)C)C.O.ON1C2C=CC=CC=2N=N1>O.C1COCC1.C(N(CC)CC)C>[CH3:1][O:2][C:3]1[C:4](=[O:29])[C:5]2[CH2:6][CH:7]([CH2:15][CH2:16][CH2:17][CH2:18][O:19][C:20]3[CH:21]=[CH:22][C:23]([C:24]([N:40]4[CH2:41][CH2:42][CH:37]([C:31]5[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=5)[CH2:38][CH2:39]4)=[O:25])=[CH:27][CH:28]=3)[CH2:8][C:9]=2[C:10](=[O:14])[C:11]=1[O:12][CH3:13]

Participants

8

Reactant 4

HCID 825094-Phenylpiperidinium chlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 18348629HCID 18348629, compound

Product 1

HCID 18348553HCID 18348553, compoundYield 56.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 4-[4-(5,6-dimethoxy-4,7-dioxoindan-2-yl)butoxy]benzoic acid (626 mg), 4-phenylpiperidinehydrochloride (617 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (598 mg), 1-hydroxybenzotriazole monohydrate (478 mg), triethylamine (1.30 ml), and THF (12 ml) was stirred at room temperature for 6 hr. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with water, 1N hydrochloric acid, water, saturated aqueous sodium bicarbonate, water, and saturated aqueous sodium chloride and dried. The solvent was removed in vacuo. The residue was recrystallized from ethyl acetate-diethyl ether to yield the entitled compound (482 mg) as crystals.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water, 1N hydrochloric acid, water, saturated aqueous sodium bicarbonate, water, and saturated aqueous sodium chloride
  3. customdried
  4. customThe solvent was removed in vacuo
  5. customThe residue was recrystallized from ethyl acetate-diethyl ether

Sources & evidence

ORD record
ord-54756c45290a469e96c3de0583111210
Source dataset
uspto-grants-2001_12
Patent number
US06326369B1

Reaction notes

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