Benzylamine → 1-Benzyl-3-(4-chloro-phenyl)-5-methyl-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridine

HRID 599901Notes

Reaction equation

HRID 599901 reaction equation
C(O[C:4]([N:6]1[CH2:11][CH2:10][C:9]2[N:12]([CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH:13]=[C:14]([C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=3)[C:8]=2[CH2:7]1)=O)C.C(OC(N1CCC(=O)CC1)=O)C.C(N)C1C=CC=CC=1.ClC1C=CC(C=C[N+]([O-])=O)=CC=1>C1C=CC=CC=1.C1(C)C=CC=CC=1>[CH2:22]([N:12]1[C:9]2[CH2:10][CH2:11][N:6]([CH3:4])[CH2:7][C:8]=2[C:14]([C:15]2[CH:16]=[CH:17][C:18]([Cl:21])=[CH:19][CH:20]=2)=[CH:13]1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

7

Reactant 4

HCID 7504BenzylamineHCID 34767Ethyl 4-oxo-1-piperidinecarboxylateHCID 95339p-Chloro-beta-nitrostyreneHCID 672694371-Benzyl-3-(4-chloro-phenyl)-1,4,6,7-tetrahydro-pyrrolo[3,2-c]pyridine-5-carboxylic acid ethyl ester

Product 1

HCID 114049551-Benzyl-3-(4-chloro-phenyl)-5-methyl-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridine

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 1140TolueneSolvent

Procedure

1-Benzyl-3-(4-chloro-phenyl)-1,4,6,7-tetrahydro-pyrrolo[3,2-c]pyridine-5-carboxylic acid ethyl ester. To a stirred solution of 3.0 g of 4-oxo-piperidine-1-carboxylic acid ethyl ester in benzene (35 mL) was added 1.91 mL of benzylamine. The mixture was heated at reflux for 24 h using a Dean-Stark apparatus. The solvent was removed to give a pale yellow oil. A portion of the crude product (0.50 g) was dissolved in toluene (4 mL) and 0.35 g of 1-chloro-4-(2-nitro-vinyl)-benzene was added, followed by 0.7 g of 4 Å molecular sieves. The resulting mixture was stirred for 12 h at RT. The mixture was then filtered through diatomaceous earth and the filtrate was washed with satd. aq. NH4Cl (3×). The combined organic extracts were dried over Na2SO4, filtered, and concentrated in vacuo. Chromatography on SiO2 (8% EtOAc/hexanes) afforded 0.25 g the title compound. TLC (SiO2, 25% EtOAc/hexanes): Rf=0.34. MS (ESI): exact mass calculated for C23H23ClN2O2, 394.14. found, m/z 395.2 [M+H]+, 397.2 [M+H]+, 417.1 [M+Na]+.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 24 h
  3. customThe solvent was removed
  4. customto give a pale yellow oil
  5. filtrationThe mixture was then filtered through diatomaceous earth
  6. washthe filtrate was washed with satd
  7. dry with materialThe combined organic extracts were dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-16c43500f22e4342a9ce3503015d3501
Source dataset
uspto-grants-2011_03
Patent number
US07897771B2

Reaction notes

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