3-(Chloromethyl)pyridine hydrochloride → HCID 58762564, compound

HRID 1453216Notes

Reaction equation

HRID 1453216 reaction equation
[CH2:1]1[CH2:11][CH2:10][N:9]2C(=N[CH2:6][CH2:7][CH2:8]2)CC1.[Cl:12][C:13]1[CH:14]=[C:15]([CH2:21][CH2:22][C:23]2([CH:31]3[CH2:35][CH2:34][CH2:33][CH2:32]3)[O:28][C:27](=[O:29])[CH2:26][C:25](=[O:30])[CH2:24]2)[CH:16]=[CH:17][C:18]=1[O:19][CH3:20].Cl.ClCC1C=NC=CC=1>C1C=CC=CC=1.C(#N)C>[Cl:12][C:13]1[CH:14]=[C:15]([CH2:21][CH2:22][C:23]2([CH:31]3[CH2:35][CH2:34][CH2:33][CH2:32]3)[O:28][C:27](=[O:29])[CH:26]([CH2:1][C:11]3[CH:10]=[N:9][CH:8]=[CH:7][CH:6]=3)[C:25](=[O:30])[CH2:24]2)[CH:16]=[CH:17][C:18]=1[O:19][CH3:20]

Participants

6

Reactant 3

HCID 233943-(Chloromethyl)pyridine hydrochlorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 160761096-(3-chloro-4-methoxyphenethyl)-6-cyclopentyl-dihydro-3H-pyran-2,4-dione

Product 1

HCID 58762564HCID 58762564, compoundYield 11.7%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 6342AcetonitrileSolvent

Procedure

DBU (55 ul, 0.367 mmol) was added to a solution of 6-[2-(3-chloro-4-methoxyphenyl)ethyl]-6-cyclopentyldihydro-2H-pyran-2,4(3H)-dione (58.6 mg, 0.167 mmol) in benzene (16.0 ml) and acetonitrile (3 ml), under an atmosphere of argon. 3-(chloromethyl)pyridine hydrochloride (27.4 mg, 0.167 mmol) was then added. The reaction mixture was stirred at room temperature for 24 hrs, after which time the mixture was filtered through a plug of Celite. The filtrate was concentrated in vacuo and the residue purified by prep HPLC to afford the title compound as a white solid (8.60 mg). 1H NMR (CDCl3): δ 1.40-1.80 (bm, 8H), 1.90 (m, 2H), 2.30 (m, 1H), 2.51 (m, 3H), 2.74 (d, J=17.27 Hz, 1H), 3.74 (m, 3H), 3.85 (s, 3H), 6.73 (d, J=8.32 Hz, 1H), 6.89 (m, 1H), 7.02 (s, 1H), 7.30 (m, 1H), 7.92 (m, 1H), 8.26 (s, 1H), 8.55 (s, 1H).

Workup

  1. filtrationafter which time the mixture was filtered through a plug of Celite
  2. concentrationThe filtrate was concentrated in vacuo
  3. customthe residue purified by prep HPLC

Sources & evidence

ORD record
ord-9a05dc066ea74c96a525f1f0cb926b76
Source dataset
uspto-grants-2009_01
Patent number
US07473790B2

Reaction notes

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