Hydrochloric Acid → HCID 22129662, compound

HRID 726818Notes

Reaction equation

HRID 726818 reaction equation
N1([CH:6]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[C:11](Cl)[CH:10]=2)CN)CCCC1.Cl.[N:18]1([CH:23]([C:32]#[N:33])[C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[C:26]([Cl:31])[CH:25]=2)[CH2:22][CH2:21][CH2:20][CH2:19]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].S([O-])([O-])(=O)=[O:41].[Na+].[Na+].Cl>O1CCCC1.C(OCC)C>[ClH:15].[Cl:31][C:26]1[CH:25]=[C:24]([CH:23]([N:18]2[CH2:22][CH2:21][CH2:20][CH2:19]2)[CH2:32][NH:33][C:6](=[O:41])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:29]=[CH:28][C:27]=1[Cl:30]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 24436Sodium SulfateHCID 16791510HCID 16791510, compoundHCID 21226445Aluminium lithium hydrideHCID 22129665HCID 22129665, compound

Product 1

HCID 22129662HCID 22129662, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

2-(Pyrrolidin-1-yl)-2-(3,4-dichlorophenyl)ethylamine. A slurry of α-Pyrrolidin-1-yl-3,4-dichlorobenzyl cyanide hydrochloride salt (4.73 g) in tetrahydrofuran (100 mL) was added to a slurry of lithium aluminum hydride (3.23 g) in tetrahydrofuran (35 mL) while maintaining a reflux. The reaction was allowed to reflux 18 hours. The reaction was cooled in an ice bath and treated with aqueous sodium sulfate. The reaction was filtered and evaporated to give a reddish-brown oil. The oil was dissolved in diethylether, treated with hydrochloric acid (g)/diethylether, and evaporated to a red oil which was used directly in subsequent reactions.

Workup

  1. temperaturewhile maintaining a reflux
  2. temperatureto reflux 18 hours
  3. temperatureThe reaction was cooled in an ice bath
  4. filtrationThe reaction was filtered
  5. customevaporated
  6. customto give a reddish-brown oil
  7. customevaporated to a red oil which

Sources & evidence

ORD record
ord-25193dad64344986b18705520de0ab77
Source dataset
uspto-grants-1998_01
Patent number
US05710169

Reaction notes

Loading…