Triethylamine → HCID 42880079, compound

HRID 917126Notes

Reaction equation

HRID 917126 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.[Cl:15][C:16]1[CH:23]=[CH:22][C:19]([CH2:20]Br)=[CH:18][CH:17]=1.C(N(CC)CC)C>C(Cl)Cl>[C:11]([O:10][C:8]([N:5]1[CH2:4][CH2:3][CH:2]([NH:1][CH2:20][C:19]2[CH:22]=[CH:23][C:16]([Cl:15])=[CH:17][CH:18]=2)[CH2:7][CH2:6]1)=[O:9])([CH3:14])([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 693291-(Bromomethyl)-4-chlorobenzeneHCID 12682914-Amino-1-Boc-piperidine

Product 1

HCID 42880079HCID 42880079, compoundYield 27.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Amino-1-N-Boc piperidine (1.80 g, 8.9 mmol) was dissolved in CH2Cl2 and 4-chlorobenzylbromide (1.84 g, 8.9 mmol) and triethylamine (1.25 mL, 8.9 mmol) were added. The solution was allowed to stir for 14 h at room temperature and evaporated in vacuo and partitioned between ether/1N NaOH. The aqueous layer was removed and the ether was washed with brine and dried over MgSO4, filtered and evaporated in vacuo, then purified by Biotage flash chromatography (5% methanol/95% methylene chloride) to yield the title compound (0.800 g, 27%). 1H-NMR (CDCl3): δ 1.26 (m, 1H), 1.44 (s, 9H), 1.83 (d, 2H), 2.63 (t, 1H), 2.78 (t, 2H), 3.46 (s, 2H), 3.78 (s, 2H), 4.00 (bs, 2H), 7.26 (bs, 4H). ESI-MS m/z: 325.1 (M+1), retention time 1.86.

Workup

  1. customevaporated in vacuo
  2. custompartitioned between ether/1N NaOH
  3. customThe aqueous layer was removed
  4. washthe ether was washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. custompurified by Biotage flash chromatography (5% methanol/95% methylene chloride)

Sources & evidence

ORD record
ord-2a2a20a62d384cbab15d3bf8272927d5
Source dataset
uspto-grants-2007_09
Patent number
US07271176B2

Reaction notes

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