Triethylamine → HCID 68634490, compound

HRID 1176513Notes

Reaction equation

HRID 1176513 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][N:6]1[C:11]2[CH:12]=[C:13]([CH2:16][O:17][CH:18]3[CH:23]([C:24]4[CH:29]=[CH:28][C:27]([O:30][CH:31]5[CH2:35][CH2:34][NH:33][CH2:32]5)=[CH:26][CH:25]=4)[CH2:22][CH2:21][N:20]([C:36]([O:38][CH2:39][C:40]4[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=4)=[O:37])[CH2:19]3)[CH:14]=[CH:15][C:10]=2[O:9][CH2:8][CH2:7]1.C(N(CC)CC)C.[CH:53]1([CH2:56][C:57](Cl)=[O:58])[CH2:55][CH2:54]1>ClCCl>[CH:53]1([CH2:56][C:57]([N:33]2[CH2:34][CH2:35][CH:31]([O:30][C:27]3[CH:28]=[CH:29][C:24]([CH:23]4[CH2:22][CH2:21][N:20]([C:36]([O:38][CH2:39][C:40]5[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=5)=[O:37])[CH2:19][CH:18]4[O:17][CH2:16][C:13]4[CH:14]=[CH:15][C:10]5[O:9][CH2:8][CH2:7][N:6]([CH2:5][CH2:4][CH2:3][O:2][CH3:1])[C:11]=5[CH:12]=4)=[CH:25][CH:26]=3)[CH2:32]2)=[O:58])[CH2:55][CH2:54]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 143262682-Cyclopropylacetyl chlorideHCID 68634962benzyl 3-[4-(3-methoxypropyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]-4-[4-(pyrrolidin-3-yloxy)phenyl]piperidine-1-carboxylate

Product 1

HCID 68634490HCID 68634490, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The solution of 0.120 g of benzyl 3-[4-(3-methoxypropyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]-4-[4-(pyrrolidin-3-yloxy)phenyl]piperidine-1-carboxylate in 4.0 ml of dichloromethane is cooled to 0° C. with stirring and admixed with 0.032 ml of triethylamine. 0.031 ml of cyclopropylacetyl chloride in 0.40 ml of dichloromethane is slowly added dropwise. Subsequently, the mixture is stirred at 0° C. over 1 hour. The reaction mixture is poured onto ice-water (20 ml) and extracted with tert-butyl methyl ether (2×20 ml). The organic phases are washed with brine (20 ml), dried over sodium sulphate and concentrated by evaporation. The title compound is obtained as a pink oil from the residue by means of flash chromatography (SiO2 60F). Rf=0.30 (200:20:1 dichloromethane-methanol-25% conc. ammonia); Rt=5.18.

Workup

  1. stirringSubsequently, the mixture is stirred at 0° C. over 1 hour
  2. additionThe reaction mixture is poured onto ice-water (20 ml)
  3. extractionextracted with tert-butyl methyl ether (2×20 ml)
  4. washThe organic phases are washed with brine (20 ml)
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-7bbfb6953c0d4b9da805d776e61442e0
Source dataset
uspto-grants-2010_11
Patent number
US07842688B2

Reaction notes

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