Triethylamine → Tert-butyl 4-(2,2-dibromovinyl)piperidine-1-carboxylate

HRID 1063369Notes

Reaction equation

HRID 1063369 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:20][C:21]([Br:24])(Br)Br.C(N(CC)CC)C.[C:32]([O:36][C:37]([N:39]1[CH2:44][CH2:43][CH:42]([CH:45]=O)[CH2:41][CH2:40]1)=[O:38])([CH3:35])([CH3:34])[CH3:33]>C(Cl)Cl>[C:32]([O:36][C:37]([N:39]1[CH2:44][CH2:43][CH:42]([CH:45]=[C:21]([Br:24])[Br:20])[CH2:41][CH2:40]1)=[O:38])([CH3:35])([CH3:33])[CH3:34]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 1514430tert-Butyl 4-formylpiperidine-1-carboxylate

Product 1

HCID 11474132Tert-butyl 4-(2,2-dibromovinyl)piperidine-1-carboxylateYield 75.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
20 °C

Procedure

A solution of 160.86 g (613.3 mmol) of triphenylphosphine in 600 ml CH2Cl2 was treated with 101.7 g (306.6 mmol) of tetrabromomethane (the reaction heated up to 32° C.) and after 50 min at 20° C., 97.8 ml (705.3 mmol) of triethylamine was added (the reaction heated up to 35° C. and the color became dark violet). After cooling (0° C.), 32.7 g (153.4 mmol) of 4-Formyl-piperidine-1-carboxylic acid tert-butyl ester in 380 ml CH2Cl2 were added slowly (20 min). The solution was stirred over night at RT, evaporated and filtered through silica gel (deactivated with hexane/Et3N; with hexane and then hexane/ether 4:1 to 1:1) to give 42.54 g (75%) of 4-(2,2-dibromo-vinyl)-piperidine-1-carboxylic acid tert-butyl ester, mp: 82.3-83.9° C., MS: 368 (MH+, 2Br).

Workup

  1. temperatureheated up to 35° C.
  2. additionwere added slowly (20 min)
  3. customevaporated
  4. filtrationfiltered through silica gel (

Sources & evidence

ORD record
ord-812b5b4d9b624fcf81d3d790b1e7f6af
Source dataset
uspto-grants-2005_11
Patent number
US06964974B2

Reaction notes

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