Triethylamine → HCID 69270089, compound

HRID 1593593Notes

Reaction equation

HRID 1593593 reaction equation
[NH2:1]/[C:2](/[CH3:6])=[CH:3]\[C:4]#[N:5].CCN(CC)CC.[CH2:14]([N:21]1[CH2:26][CH2:25][C:24](=O)[CH2:23][CH2:22]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(Cl)Cl.Cl[Ti](Cl)(Cl)Cl>[NH2:1]/[C:2](/[CH3:6])=[C:3](\[C:24]1[CH2:25][CH2:26][N:21]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:22][CH:23]=1)/[C:4]#[N:5]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 192201-Benzyl-4-piperidoneHCID 5325263(2Z)-3-Amino-2-butenenitrile

Product 1

HCID 69270089HCID 69270089, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A solution of β-aminocrotononitrile (12 g, 147 mmol) and NEt3 (37 mL, 266 mmol) in CH2Cl2 (150 mL) was cooled with an ice bath to 0°. TiCl4 (7.9 mL, 72 mmol) in CH2Cl2 (100 mL) was added slowly with stirring followed by N-benzyl-4-piperidone (21.4 mL, 120 mmol) in one portion. The mixture was stirred for 24 h at ambient temperature and the volatiles were removed under reduced pressure. Ethly ether (400 mL) was added, and the resulting mixture was stirred vigorously until the residue was ground to a fine powder. The powder was filtered off and washed with ethyl ether (400 mL) and evaporation of the solvent afforded (E)-3-amino-2-(1-benzyl-1,2,3,6-tetrahydro-pyridin-4-yl)-but-2-enenitrile as an oil (20 g, 70%), which was used without further purification.

Workup

  1. stirringThe mixture was stirred for 24 h at ambient temperature
  2. customthe volatiles were removed under reduced pressure
  3. additionEthly ether (400 mL) was added
  4. stirringthe resulting mixture was stirred vigorously until the residue
  5. filtrationThe powder was filtered off
  6. washwashed with ethyl ether (400 mL) and evaporation of the solvent

Sources & evidence

ORD record
ord-421fb233694048b780a89e11c92339b2
Source dataset
uspto-grants-2007_11
Patent number
US07297700B2

Reaction notes

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