Hydrochloric Acid → HCID 13565190, compound

HRID 904902Notes

Reaction equation

HRID 904902 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.[O:7]([C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=1)[CH:17]=O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[C-:22]#[N:23].[Na+]>O.ClCCl>[N:1]1([CH:17]([C:16]2[CH:19]=[CH:20][CH:21]=[C:14]([O:7][C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH:15]=2)[C:22]#[N:23])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8929Sodium CyanideHCID 31268PyrrolidineHCID 382843-Phenoxybenzaldehyde

Product 1

HCID 13565190HCID 13565190, compoundYield 89.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of pyrrolidine (2.13 g, 30 mmole) in water (10 ml) was neutralised with concentrated hydrochloric acid. 3-Phenoxybenzaldehyde (3.96 g; 20 mmole) was added to the stirred solution followed by sodium cyanide (1.5 g; 30 mmole) and "Teric" N8 (5 drops of a 10% aqueous solution). The mixture was stirred vigorously for a period of 1 hour and then dichloromethane (50 ml) was added. The organic phase was separated, washed with water and dried over anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure to give the title compound as a yellow oil (5.0 g). Proton magnetic resonance spectrum (CDCl3 ; δ in ppm): 1.8 (4H, m, pyrrolidine ring β-protons); 2.6 (4H, m, pyrrolidine ring α-protons); 5.0 (1H, s, CH); 7.0-7.6 (9H, m, aromatic protons). Infra-red spectrum (liquid film; νmax in cm-1): 2950 (m) (m); 2800(m); 1580(s); 1480(s); 1240(s); 840(m); 740(m).

Workup

  1. customThe organic phase was separated
  2. washwashed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-8575d2b0f0bf43d6953739254a5f4fef
Source dataset
uspto-grants-1983_12
Patent number
US04420614

Reaction notes

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