Potassium Carbonate → HCID 18437105, compound

HRID 242587Notes

Reaction equation

HRID 242587 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([OH:24])[CH2:13][CH2:12][NH:11][CH2:10][C:9]2([CH2:15][O:16][CH2:17][CH2:18][N:19]([CH2:22][CH3:23])[CH2:20][CH3:21])[CH3:14])=[CH:4][CH:3]=1.[C:25]([O-:28])([O-])=[O:26].[K+].[K+].BrCC[CH:34]=[C:35]1[C:41]2C=CC=NC=2COC2C=CC(C(O)(C)C)=C[C:36]1=2>C(#N)C.O>[C:35]([O:28][C:25]([N:11]1[CH2:12][CH2:13][C:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)([OH:24])[C:9]([CH2:15][O:16][CH2:17][CH2:18][N:19]([CH2:22][CH3:23])[CH2:20][CH3:21])([CH3:14])[CH2:10]1)=[O:26])([CH3:41])([CH3:36])[CH3:34]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 23137056HCID 23137056, compoundHCID 666859992-[5-(3-Bromo-propylidene)-5,1 1-dihydro-10-oxa-1-aza-dibenzo[a,d]cyclohepten-7-yl]-propan-2-ol

Product 1

HCID 18437105HCID 18437105, compound

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

To a solution of 4-(4-chloro-phenyl)-3-(2-diethylamino-ethoxymethyl)-3-methyl-piperidin-4-ol in acetonitrile/water (8:2) (3.2 mL) was added K2CO3 and 2-[5-(3-bromo-propylidene)-5,11-dihydro-10-oxa-1-aza-dibenzo[a,d]cyclohepten-7-yl]-propan-2-ol. The solution was allowed to stir at room temperature for 48 h. The reaction was concentrated down and partitioned between EtOAc/H2O, extracted with EtOAc (3×). The organics were collected, dried over MgSO4, filtered and evaporated in vacuo, then purified by Biotage flash chromatography (5% methanol/95% methylene chloride to 10% methanol/90% methylene chloride to 15% methanol/85% methylene chloride) to yield the title compound. 1H-NMR (CDCl3): 0.50 (s, 3H), 0.97 (t, 6H), 1.52 (s, 6H), 2.40-2.66 (m, 12H), 3.16-3.30 (m, 6H), 5.32 (bs, 2H), 6.06 (t, 1H), 6.80 (t, 1H), 7.20 (dd, 1H), 7.29 (dd, 1H), 7.29-7.31 (m, 6H), 7.58 (d, 2H), 8.51 (d, 1H). δ ESI-MS m/z: 648 (M+1), retention time 1.19.

Workup

  1. concentrationThe reaction was concentrated down
  2. custompartitioned between EtOAc/H2O
  3. extractionextracted with EtOAc (3×)
  4. customThe organics were collected
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. custompurified by Biotage flash chromatography (5% methanol/95% methylene chloride to 10% methanol/90% methylene chloride to 15% methanol/85% methylene chloride)

Sources & evidence

ORD record
ord-1202d51229a74b88b71b8e629fafa8d4
Source dataset
uspto-grants-2014_02
Patent number
US08653096B2

Reaction notes

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