N-Methylbenzylamine → HCID 68688967, compound

HRID 2354049Notes

Reaction equation

HRID 2354049 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][C:14]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)([C:17](O)=[O:18])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O=S(Cl)Cl.[CH3:30][NH:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.CCN(C(C)C)C(C)C>C(Cl)(Cl)Cl>[CH2:1]([O:8][C:9]([N:11]1[CH2:12][CH2:13][C:14]([C:17](=[O:18])[N:31]([CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH3:30])([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:15][CH2:16]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 7669N-MethylbenzylamineHCID 24386Thionyl ChlorideHCID 81531DiisopropylethylamineHCID 227417981-(Benzyloxycarbonyl)-4-phenylpiperidine-4-carboxylic acid

Product 1

HCID 68688967HCID 68688967, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A mixture of 4-phenyl-piperidine-1,4-dicarboxylic acid monobenzyl ester (3.39 g, 10 mmol) and SOCl2 (7 mL, 100 mmol) in CHCl3 (150 mL) is heated at reflux for 3 h. The solvent and excess SOCl2 are evaporated into a cold trap and the residue is redissolved in CHCl3 (50 mL). The solution is added to a solution of methylbenzylamine (1.45 g, 12 mmol) and DIPEA (2 mL, 12 mmol) in cold (0° C.) CHCl3 (100 mL). The mixture is stirred for 15 h at r.t. and then quenched with sat. aq. Na2CO3 (50 mL). The phases are separated and the aq. phase is extracted with CH2Cl2 (2×50 mL). The combined organic extracts are washed with 1N aq. HCl (50 mL) and sat. aq. NaCl (50 mL), dried (Na2SO4), filtered and evaporated. The residue is purified by FC (SiO2, heptane-EtOAc) to provide the title compound.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 3 h
  3. customThe solvent and excess SOCl2 are evaporated into a cold trap
  4. dissolutionthe residue is redissolved in CHCl3 (50 mL)
  5. customquenched with sat. aq. Na2CO3 (50 mL)
  6. customThe phases are separated
  7. extractionthe aq. phase is extracted with CH2Cl2 (2×50 mL)
  8. washThe combined organic extracts are washed with 1N aq. HCl (50 mL) and sat. aq. NaCl (50 mL)
  9. dry with materialdried (Na2SO4)
  10. filtrationfiltered
  11. customevaporated
  12. customThe residue is purified by FC (SiO2, heptane-EtOAc)

Sources & evidence

ORD record
ord-68d5598eef3c4ebb978b700de8a97c42
Source dataset
uspto-grants-2010_07
Patent number
US07750161B2

Reaction notes

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