Triethylamine → HCID 25120927, compound

HRID 1664692Notes

Reaction equation

HRID 1664692 reaction equation
FC(F)(F)C([O-])=O.[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:16]=[C:17]([C@H:20]3[CH2:25][CH2:24][CH2:23][CH2:22][NH2+:21]3)[S:18][CH:19]=2)=[CH:11][CH:10]=1.C(N(CC)CC)C.CN(C1C=CC=CN=1)C.[O:42]([CH2:49][C:50](Cl)=[O:51])[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1>ClCCl>[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[N:16]=[C:17]([C@H:20]3[CH2:25][CH2:24][CH2:23][CH2:22][N:21]3[C:50](=[O:51])[CH2:49][O:42][C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)[S:18][CH:19]=2)=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 69703Phenoxyacetyl chlorideHCID 86625165HCID 86625165, compound

Product 1

HCID 25120927HCID 25120927, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (R)-2-[4-(4-chloro-phenyl)-thiazol-2-yl]-piperidinium trifluoroacetate (0.077 g, 0.20 mmol) in dry dichloromethane (2 mL) under argon was treated with triethylamine (0.079 g, 0.11 mL), dimethylaminopyridine (0.002 g, 0.020 mmol) and phenoxyacetyl chloride (0.033 g, 0.20 mmol). The mixture was stirred at room temperature for 16 h. The mixture was washed with water and saturated sodium chloride. The organic phase was dried over sodium sulphate and evaporated. The residual oil was purified by preparative HPLC: Column: YMC-Pack Pro C18 RS, 20×50 mm, S-5 um, 8 nm, No 200504707(W); Gradient: 0-0.4 min: 30% acetonitrile in (water+0.1% HCO2H), 0.4-2 min: increse of acetonitrile fraction from 30% to 95%, 2.4-3.7 min: 95% acetonitrile, 3.7-3.8 min: decrease of acetonitrile fraction from 95% to 30%; Program end at 4 min; Flow: 30 ml/min. 1-{(R)-2-[4-(4-Chloro-phenyl)-thiazol-2-yl]-piperidin-1-yl}-2-phenoxy-ethanone was obtained after lyophilization as a light yellow oil (0.037 g, 46%), MS (ISP): 413.1, 415.4 (M+H)+.. 1H-NMR (CDCl3, 300 MHz): 7.81 (2H, d), 7.38 (3H, m), 7.27 (2H, m), 6.98 (3H, m), 6.11+5.58 (1H, bs), 4.82 (2H, m), 4.56+3.91 (1H, bd), 3.36+2.86 (1H, bt), 2.59 (1H, m), 1.75 (5H, m).

Workup

  1. washThe mixture was washed with water and saturated sodium chloride
  2. dry with materialThe organic phase was dried over sodium sulphate
  3. customevaporated
  4. customThe residual oil was purified by preparative HPLC
  5. custom0-0.4 min
  6. customin (water+0.1% HCO2H), 0.4-2 min
  7. customfrom 30% to 95%, 2.4-3.7 min
  8. custom95% acetonitrile, 3.7-3.8 min
  9. waitProgram end at 4 min

Sources & evidence

ORD record
ord-6fdc8ea63add4d2db5d2a99b7514cd39
Source dataset
uspto-grants-2011_10
Patent number
US08039487B2

Reaction notes

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