Hydrochloric Acid → HCID 22266037, compound

HRID 489592Notes

Reaction equation

HRID 489592 reaction equation
[C:1]1([C:7]#[C:8][C:9]2[CH:10]=[C:11]([C:15]([N:17]3[CH2:22][CH2:21][CH:20]([C:23]4[CH:24]=[C:25]([CH:28]=[CH:29][CH:30]=4)[C:26]#[N:27])[CH2:19][CH2:18]3)=[O:16])[CH:12]=[N:13][CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[ClH:31]>C(OCC)(=O)C>[ClH:31].[ClH:31].[C:1]1([C:7]#[C:8][C:9]2[CH:10]=[C:11]([C:15]([N:17]3[CH2:18][CH2:19][CH:20]([C:23]4[CH:24]=[C:25]([CH:28]=[CH:29][CH:30]=4)[CH2:26][NH2:27])[CH2:21][CH2:22]3)=[O:16])[CH:12]=[N:13][CH:14]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 671944903-[1-(5-Phenylethynyl-pyridine-3-carbonyl)-piperidin-4-yl]-benzonitrile

Product 1

HCID 22266037HCID 22266037, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3-[1-(5-phenylethynyl-pyridine-3-carbonyl)-piperidin-4-yl]-benzonitrile (0.15 g, 0.25 mmol) in ethyl acetate (20 ml) was cooled to 0° C. and then saturated with hydrogen chloride gas. The reaction mixture was stirred at ambient temperature for 4 hours and then concentrated to dryness under vacuum. The residue was treated with ethyl acetate (10 ml) and the solvent removed under vacuum. This process was repeated twice to give 3-[1-(5-phenylethynyl-pyridine-3-carbonyl)-piperidin-4-yl]-benzylamine di-hydrochloride as a white solid (0.11 g). 1H NMR [(CD3)2SO, 500 MHz]: δ 8.83 (s, 1H), 8.63 (s, 1H), 8.08 (s, 1H), 7.61 (m, 2H), 7.45 (m, 3H), 7.44 (s, 1H), 7.37 (m, 3H), 4.64 (br m, 1H), 4.00 (m, 2H), 3.62 (br m, 1H), 3.25 (br m, 1H), 2.90 (br m, 2H), 1.88 (br m, 1H), 1.70 (m, 3H). MS(EI): 396(M++H).

Workup

  1. concentrationconcentrated to dryness under vacuum
  2. additionThe residue was treated with ethyl acetate (10 ml)
  3. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-d555b10cb21c41cb85357ade733e8a06
Source dataset
uspto-grants-2005_12
Patent number
US06977263B2

Reaction notes

Loading…