Triethylamine → HCID 59006937, compound

HRID 1174536Notes

Reaction equation

HRID 1174536 reaction equation
[CH:1]([N:4]([CH:16]([CH3:18])[CH3:17])[C:5]([C:7]1[CH:15]=[CH:14][C:10]([C:11](Cl)=[O:12])=[CH:9][CH:8]=1)=[O:6])([CH3:3])[CH3:2].[CH2:19]([O:21][C:22]1[CH:23]=[C:24]([C@@H:30]2[C@H:35]([NH2:36])[CH2:34][CH2:33][O:32][CH2:31]2)[CH:25]=[CH:26][C:27]=1[O:28][CH3:29])[CH3:20].C(N(CC)CC)C>ClCCl>[CH2:19]([O:21][C:22]1[CH:23]=[C:24]([C@@H:30]2[C@H:35]([NH:36][C:11](=[O:12])[C:10]3[CH:14]=[CH:15][C:7]([C:5]([N:4]([CH:16]([CH3:18])[CH3:17])[CH:1]([CH3:3])[CH3:2])=[O:6])=[CH:8][CH:9]=3)[CH2:34][CH2:33][O:32][CH2:31]2)[CH:25]=[CH:26][C:27]=1[O:28][CH3:29])[CH3:20]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 18363041HCID 18363041, compoundHCID 59006942HCID 59006942, compound

Product 1

HCID 59006937HCID 59006937, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 1 equivalent 4-diisopropylcarbamoyl-benzoyl chloride (prepared from N,N-diisopropyl-terephthalamic acid and thionyl chloride) in dichloromethane is added dropwise at RT in the course of 10 min. to a solution of 1 equivalent of (3R,4R)-3-(3-ethoxy-4-methoxy-phenyl)-tetrahydro-pyran-4-ylamine in dichloromethane and 1.1 equivalents of triethylamine. After stirring for about 2 h, the mixture is extracted with saturated sodium hydrogencarbonate solution, and the organic phase is washed a further two times with water and dried over sodium sulfate. The viscous residue remaining after concentration is purified by column chromatography on SiO2 (dichloromethane/ethyl acetate 85/15 vol/vol). The main product fraction concentrated in vacuo affords a brownish solid foaming residue which is used for the next reaction step without further treatment.

Workup

  1. extractionthe mixture is extracted with saturated sodium hydrogencarbonate solution
  2. washthe organic phase is washed a further two times with water
  3. dry with materialdried over sodium sulfate
  4. concentrationafter concentration
  5. customis purified by column chromatography on SiO2 (dichloromethane/ethyl acetate 85/15 vol/vol)
  6. concentrationThe main product fraction concentrated in vacuo
  7. customaffords a brownish solid foaming residue which
  8. customis used for the next reaction step without further treatment

Sources & evidence

ORD record
ord-1453450d51d0415bb85569a2721880f8
Source dataset
uspto-grants-2010_11
Patent number
US07838521B2

Reaction notes

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