Triethylamine → HCID 57964436, compound

HRID 2403536Notes

Reaction equation

HRID 2403536 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([CH2:11][CH2:12][N:13]3[CH2:18][CH2:17][N:16]([C:19]4[CH:20]=[C:21]([CH:23]=[CH:24][CH:25]=4)[NH2:22])[CH2:15][CH2:14]3)[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.C(N(CC)CC)C.Cl[C:34]([O:36][CH2:37][CH3:38])=[O:35]>ClCCl>[CH2:37]([O:36][C:34](=[O:35])[NH:22][C:21]1[CH:23]=[CH:24][CH:25]=[C:19]([N:16]2[CH2:15][CH2:14][N:13]([CH2:12][CH2:11][CH:8]3[CH2:7][CH2:6][C:5]4([O:4][CH2:3][CH2:2][O:1]4)[CH2:10][CH2:9]3)[CH2:18][CH2:17]2)[CH:20]=1)[CH3:38]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 57964805HCID 57964805, compound

Product 1

HCID 57964436HCID 57964436, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled solution of 1 g (3 mmol) of 3-{4-[2-(1,4-dioxaspiro[4.5]dec-8-yl)ethyl]piperazin-1-yl}aniline in 30 mL of dichloromethane and 0.3 g (3 mmol) of triethylamine, is slowly added 0.32 g (3 mmol) of ethyl chloroformate. The mixture is stirred overnight at room temperature then concentrated under reduced pressure. The product is dissolved in ethyl acetate, washed twice with water, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The oily residue is purified over 10 g of silica gel (eluant dichloromethane/methanol 95/5) to give 0.35 g (29%) of (3-{4-[2-(1,4-dioxaspiro[4.5]dec-8-yl)ethyl]piperazin-1-yl}phenyl)carbamic acid ethyl ester.

Workup

  1. concentrationthen concentrated under reduced pressure
  2. dissolutionThe product is dissolved in ethyl acetate
  3. washwashed twice with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe oily residue is purified over 10 g of silica gel (eluant dichloromethane/methanol 95/5)

Sources & evidence

ORD record
ord-6a95ab16b53346db9625d41da9641cbd
Source dataset
uspto-grants-2014_08
Patent number
US08802678B2

Reaction notes

Loading…