Triethylamine → 7-(4-Bromobenzyl)-2-oxa-7-azaspiro[3.5]nonane

HRID 1505931Notes

Reaction equation

HRID 1505931 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6]Br)=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH2:17]1[C:20]2([CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)[CH2:19][O:18]1>C1COCC1>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][N:23]2[CH2:24][CH2:25][C:20]3([CH2:17][O:18][CH2:19]3)[CH2:21][CH2:22]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 685274-Bromobenzyl bromideHCID 219552842-Oxa-7-azaspiro[3.5]nonane

Product 1

HCID 582664907-(4-Bromobenzyl)-2-oxa-7-azaspiro[3.5]nonaneYield 97.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-bromobenzyl bromide (0.26 g, 1.04 mmol), triethylamine (0.21 mL, 2.07 mmol) and 2-oxa-7-azaspiro[3.5]nonane (0.50 g, 2.07 mmol) in THF (20 mL) was heated under reflux for 5 h. The reaction mixture was cooled to ambient temperature, the solid removed by filtration and the filtrate was concentrated under reduced pressure. The resultant residue was loaded onto an SCX-2 cartridge (10 g) and eluted with 2N ammonia in MeOH to afford the title compound (0.30 g, 97%). 1H NMR (CDCl3, 300 MHz): 7.47-7.41 (m, 2H), 7.19 (d, J=8.1 Hz, 2H), 4.40 (s, 4H), 3.45-3.40 (m, 2H), 2.38-2.28 (s, 2H), 1.92-1.86 (s, 4H). LCMS (Method B): RT=1.89 min, M+H+=296/298.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 5 h
  3. customthe solid removed by filtration
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. washeluted with 2N ammonia in MeOH

Sources & evidence

ORD record
ord-8231825e9dda4587805100c2dd14e434
Source dataset
uspto-grants-2015_12
Patent number
US09216980B2

Reaction notes

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