Triethylamine → 1-(4-Cyanophenyl)-4-[4-(methoxycarbonylmethyl)-piperidinomethyl]-piperidine

HRID 1757008Notes

Reaction equation

HRID 1757008 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][CH:12]([CH2:15]I)[CH2:11][CH2:10]2)=[CH:5][CH:4]=1)#[N:2].Cl.[CH3:18][O:19][C:20](=[O:28])[CH2:21][CH:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1.C(N(CC)CC)C>CN(C)C=O>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][CH:12]([CH2:15][N:25]3[CH2:26][CH2:27][CH:22]([CH2:21][C:20]([O:19][CH3:18])=[O:28])[CH2:23][CH2:24]3)[CH2:11][CH2:10]2)=[CH:5][CH:4]=1)#[N:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 18423605Methyl (piperidin-4-yl)acetate--hydrogen chloride (1/1)HCID 193914561-(4-Cyanophenyl)-4-iodomethyl-piperidine

Product 1

HCID 193915461-(4-Cyanophenyl)-4-[4-(methoxycarbonylmethyl)-piperidinomethyl]-piperidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

A suspension of 2.18 g of 1-(4-cyanophenyl)-4-iodomethyl-piperidine (mixture from Example XXV), 1.26 g of methyl-4-piperidyl-acetate-hydrochloride and 1.35 g of triethylamine in 150 ml of dimethylformamide is heated to 130° C. for 24 hours. After cooling, the solvent is removed under reduced pressure and the residue is chromatographed over silica gel with methylene chloride/methanol (30:1). The solvent is removed under reduced pressure and the crude product is used for the next stage of synthesis without any further purification.

Workup

  1. temperatureAfter cooling
  2. customthe solvent is removed under reduced pressure
  3. customthe residue is chromatographed over silica gel with methylene chloride/methanol (30:1)
  4. customThe solvent is removed under reduced pressure
  5. customthe crude product is used for the next stage of synthesis without any further purification

Sources & evidence

ORD record
ord-a4f35610b9dd44dda69d7a616a37597c
Source dataset
uspto-grants-1995_08
Patent number
US05442064

Reaction notes

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