Ammonium Chloride → tert-Butyl 4-{4-[(Z)-2-(naphthalen-1-yl)ethenyl]-1,3-thiazol-2-yl}piperidine-1-carboxylate

HRID 549941Notes

Reaction equation

HRID 549941 reaction equation
[Cl-].[C:2]1([CH2:12][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][CH:3]=1.CC(C)([O-])C.[K+].[CH:38]([C:40]1[N:41]=[C:42]([CH:45]2[CH2:50][CH2:49][N:48]([C:51]([O:53][C:54]([CH3:57])([CH3:56])[CH3:55])=[O:52])[CH2:47][CH2:46]2)[S:43][CH:44]=1)=O.[Cl-].[NH4+]>O1CCCC1>[C:2]1(/[CH:12]=[CH:38]\[C:40]2[N:41]=[C:42]([CH:45]3[CH2:46][CH2:47][N:48]([C:51]([O:53][C:54]([CH3:57])([CH3:56])[CH3:55])=[O:52])[CH2:49][CH2:50]3)[S:43][CH:44]=2)[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 2734113(1-Naphthylmethyl)triphenylphosphonium chlorideHCID 7172298tert-Butyl 4-(4-formyl-1,3-thiazol-2-yl)piperidine-1-carboxylateHCID 23665647Potassium tert-butoxide

Product 1

HCID 67156180tert-Butyl 4-{4-[(Z)-2-(naphthalen-1-yl)ethenyl]-1,3-thiazol-2-yl}piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Under argon, (1-naphthylmethyl)triphenylphosphonium chloride (2.96 g) is dissolved in 20 ml of tetrahydrofuran and cooled to 0° C., and potassium tert.-butoxide (757 mg) is added, whereupon the colour of the solution changes to dark-red. After 10 min of stirring, tert-butyl 4-(4-formyl-1,3-thiazol-2-yl)piperidine-1-carboxylate (1.00 g) is added. The mixture is stirred at 0° C. for another 30 min and then slowly warmed to room temperature. After a further 20 min, saturated ammonium chloride solution is added, and the aqueous phase is separated off. After extraction of the aqueous phase with ethyl acetate, the combined organic phases are dried over sodium sulphate and concentrated under reduced pressure. After chromatographic purification, this gives tert-butyl 4-{4-[(Z)-2-(naphthalen-1-yl)ethenyl]-1,3-thiazol-2-yl}piperidine-1-carboxylate (1.2 g, Z isomer).

Workup

  1. stirringThe mixture is stirred at 0° C. for another 30 min
  2. temperatureslowly warmed to room temperature
  3. waitAfter a further 20 min
  4. customthe aqueous phase is separated off
  5. extractionAfter extraction of the aqueous phase with ethyl acetate
  6. dry with materialthe combined organic phases are dried over sodium sulphate
  7. concentrationconcentrated under reduced pressure
  8. customAfter chromatographic purification

Sources & evidence

ORD record
ord-0d049a1637d04d5aaeef52b4dda90224
Source dataset
uspto-grants-2011_05
Patent number
US07943774B2

Reaction notes

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