Hydrochloric Acid → HCID 22129662, compound

HRID 726817Notes

Reaction equation

HRID 726817 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([N:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)[CH2:10][NH2:11])[CH:5]=[CH:6][C:7]=1[Cl:8].[C:17](Cl)(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(N(CC)CC)C.Cl>ClCCl.C(OCC)C.O>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([N:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)[CH2:10][NH:11][C:17](=[O:24])[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 16791510HCID 16791510, compound

Product 1

HCID 22129662HCID 22129662, compoundYield 17.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×HCID 6344DichloromethaneSolvent2×

Procedure

2-(3,4-Dichlorophenyl)-2-(pyrrolidin-1-yl)ethylamine (2.46 g), benzoyl chloride (1.34 g) and triethylamine (1.92 g) were stirred in dichloromethane (25 mL) at 23° C., for 48 hours. The reaction was poured into water, and the seperated organic layer was dried, and evaporated to a brown oil (2.85 g). Chromatography, with chloroform (1200 mL) and then methanol:chloroform (5:95) as the eluent, gave an oil. Trituration of the oil with diethylether gave a white solid which was dissolved in dichloromethane and treated with hydrochloric acid (g)/diethylether. The solution was evaporated to give the title compound as a white glass (330 mg); mp 129° C. (after resolidifing); MS: m/z=636(M+1l); NMR: 1.78 (m, 4), 2.54 (m,4), 3.5 (m,2), 4 (m,1), 6.16 (broad s,1), 7.21 (m,1), 7.42 (m,5), 7.62 (m,2): Analysis Calculated: C, 55.22; H, 5.49; N, 6.78; Found: C, 55.21; H, 5.24; N, 6.59.

Workup

  1. customthe seperated organic layer was dried
  2. customevaporated to a brown oil (2.85 g)
  3. customChromatography, with chloroform (1200 mL) and then methanol:chloroform (5:95) as the eluent, gave an oil
  4. customThe solution was evaporated

Sources & evidence

ORD record
ord-46dc21d9893c4808817053e47b9359db
Source dataset
uspto-grants-1998_01
Patent number
US05710169

Reaction notes

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