Diisopropylethylamine → Ammonia

HRID 1459427Notes

Reaction equation

HRID 1459427 reaction equation
Cl.[NH2:2][C:3]1C=[CH:14][C:6]([O:7]CC(OCC)=O)=[CH:5][C:4]=1C.C1C[N:20]([C:22](Cl)=[N+:23]2[CH2:27][CH2:26][CH2:25][CH2:24]2)CC1.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C.CO.C(Cl)(Cl)Cl>C(Cl)Cl.CCOC(C)=O>[NH3:2].[NH2:20][C:22]([NH2:23])=[O:7].[NH:2]1[CH2:3][CH2:4][CH2:5][CH2:6][CH2:14]1.[NH:23]1[CH2:22][CH2:27][CH2:26][CH2:25][CH2:24]1

Participants

8

Reactant 4

HCID 81531DiisopropylethylamineHCID 27366521-(Chloro-1-pyrrolidinylmethylene)pyrrolidinium HexafluorophosphateHCID 21584188Chloroform methanolHCID 70346506Acetic acid,(4-amino-3-methylphenoxy)-,ethyl ester hydrochloride

Product 2

HCID 222AmmoniaHCID 21223922Bis piperidine urea

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

20-2 (486 mg; 1.6 mmol) and 10-4 (250 mg, 1.6 mmol) were dissolved in CH2Cl2. PYCLU (1.8 mmol, 634 mg) was added, followed by diisopropylethylamine (6.4 mmol, 1.1 mL). The reaction is stirred for 2 days. The reaction mixture is diluted with EtOAc and washed with H2 O, 10% KHSO4, sat NaHCO3 and brine. The organic layer is dried (MgSO4), filtered and concentrated to yield a tan oil. Flash chromatography (10% MeOH/CHCl3 sat NH3) yielded desired product (20-3) plus bis piperidine urea by-product. This material is triturated with hexane to remove most of the by-product.

Workup

  1. washwashed with H2 O, 10% KHSO4
  2. dry with materialThe organic layer is dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto yield a tan oil

Sources & evidence

ORD record
ord-ea8570e7460a4bcfbb5a8b6aeeeb0f7f
Source dataset
uspto-grants-1998_12
Patent number
US05854245

Reaction notes

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