Triethylamine → HCID 806418, compound

HRID 1505899Notes

Reaction equation

HRID 1505899 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6]Br)=[CH:4][CH:3]=1.[NH:10]1[CH2:15][CH2:14][CH:13]([N:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)[CH2:12][CH2:11]1.C(N(CC)CC)C>C1COCC1.O>[NH3:10].[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][N:10]2[CH2:15][CH2:14][CH:13]([N:16]3[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)[CH2:12][CH2:11]2)=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 8471Triethylamine2×HCID 685274-Bromobenzyl bromideHCID 7957244-Morpholinopiperidine

Product 2

HCID 222AmmoniaHCID 806418HCID 806418, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

4-Bromobenzyl bromide (0.5 g, 2.0 mmol) was stirred with 4-piperidin-4-yl-morpholine (0.67 g, 4.0 mmol) and triethylamine (0.42 mL, 3.0 mmol) in THF (20 mL) at ambient temperature for 28 h then a further 1.5 eq of triethylamine was added and stirring continued for 16 h. The mixture was diluted with water (50 mL) and extracted with ethyl acetate (50 mL). The organic phase was separated, dried over anhydrous sodium sulfate, filtered and evaporated in vacuo. The resultant residue was purified by flash chromatography (silica, 12 g column, ISCO, 0-100% ethyl acetate in cyclohexane then 0-10% (2N ammonia in methanol) in DCM) to afford the title compound as an off-white solid (0.62 g, 92%). 1H NMR (CDCl3, 400 MHz): 7.44-7.40 (m, 2H), 7.21-7.15 (m, 2H), 3.74-3.69 (m, 4H), 3.42 (s, 2H), 2.93-2.85 (m, 2H), 2.56-2.50 (m, 4H), 2.22-2.13 (m, 1H), 2.00-1.91 (m, 2H), 1.82-1.74 (m, 2H), 1.59-1.47 (m, 2H).

Workup

  1. extractionextracted with ethyl acetate (50 mL)
  2. customThe organic phase was separated
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe resultant residue was purified by flash chromatography (silica, 12 g column, ISCO, 0-100% ethyl acetate in cyclohexane

Sources & evidence

ORD record
ord-ff3c8cde43b241dea2056157c59b6e6d
Source dataset
uspto-grants-2015_12
Patent number
US09216980B2

Reaction notes

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