Piperidine → HCID 20137131, compound

HRID 280178Notes

Reaction equation

HRID 280178 reaction equation
[CH3:1][C:2]1([CH3:14])[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[O:11][CH3:12])[CH:3]1O.CS(Cl)(=O)=O.[NH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1.C(=O)(O)[O-].[Na+]>C(Cl)Cl.C(N(CC)CC)C>[CH3:1][C:2]1([CH3:14])[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[O:11][CH3:12])[CH:3]1[N:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

7

Reactant 4

HCID 8082PiperidineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 20137123HCID 20137123, compound

Product 1

HCID 20137131HCID 20137131, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
0 °C

Procedure

Triethylamine (10 ml) is added to a stirred solution of the 1-hydroxy indane of Step 2. above (8.4 g) in methylene chloride (190 ml) at RT under nitrogen; the mixture is cooled to 0° C. and methanesulfonyl chloride (4 ml) is added. The mixture is stirred for three hours at RT, cooled to 0° C., piperidine (128 ml) added and stirred at RT overnight. Sat'd aq. sodium bicarbonate is added to the mixture and the organic phase separated, washed with aq. sodium bicarbonate, sat'd NaCl, dried, filtered and the filtrate evaporated in vacuo affording the desired product as an oil.

Workup

  1. customat RT
  2. temperaturecooled to 0° C.
  3. stirringstirred at RT overnight
  4. customthe organic phase separated
  5. washwashed with aq. sodium bicarbonate
  6. customdried
  7. filtrationfiltered
  8. customthe filtrate evaporated in vacuo

Sources & evidence

ORD record
ord-00aad20b01024b28b35d8cd9f127559c
Source dataset
uspto-grants-1986_05
Patent number
US04588719

Reaction notes

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