Potassium Carbonate → HCID 66757658, compound

HRID 917128Notes

Reaction equation

HRID 917128 reaction equation
[ClH:1].Cl[C:3]1[CH:18]=[CH:17][C:6]([CH2:7][N:8](CC)[CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[CH:5][CH:4]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:26][CH2:27][CH:28]=[C:29]1[C:35]2[CH:36]=[CH:37][CH:38]=[N:39][C:34]=2[CH2:33][O:32][C:31]2[CH:40]=[CH:41][C:42]([C:44]([OH:47])([CH3:46])[CH3:45])=[CH:43][C:30]1=2.[C:48](#N)[CH3:49].O>>[Cl:1][C:5]1[CH:4]=[CH:3][C:18]([CH2:17][CH2:6][CH2:7][NH:8][CH:9]2[CH2:10][CH2:11][N:12]([CH2:26][CH2:27][CH:28]=[C:29]3[C:35]4[CH:36]=[CH:37][CH:38]=[N:39][C:34]=4[CH2:33][O:32][C:31]4[CH:40]=[CH:41][C:42]([C:44]([OH:47])([CH3:46])[CH3:45])=[CH:43][C:30]3=4)[CH2:13][CH2:14]2)=[CH:49][CH:48]=1

Participants

5

Reactant 4

HCID 11430Potassium CarbonateHCID 18373917Acetonitrile--water (1/1)HCID 23137082HCID 23137082, 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 66757658HCID 66757658, compoundYield 60%

Procedure

To a solution of (4-chloro-benzyl)-ethyl-piperidin-4-yl-amine hydrochloride (0.200 g, 0.83 mmol) in acetonitrile/water (8:2) (8 mL) was added K2CO3 (0.476 g, 3.4 mmol) and 2-[5-(3-bromo-propylidene)-5,11-dihydro-10-oxa-1-aza-dibenzo[a,d]cyclohepten-7-yl]-propan-2-ol (0.282 g, 7.5 mmol). The solution was allowed to stir at room temperature for 48 h. The reaction was concentrated 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 yield the title compound (0.240 g, 60%). 1H-NMR (CDCl3): δ 0.988 (t, 3H), 1.57 (s, 6H), 1.67 (d, 2H), 1.85 (t, 2H), 2.32–2.46 (m, 5H), 2.51 (q, 2H), 2.84 (d, 2H), 3.47 (s, 2H), 3.56 (s, 2H), 5.29 (bs, 2H), 6.07 (t, 1H), 6.80 (d, 1H), 7.21–7.28 (m, 6H), 7.42 (s, 1H), 7.56 (d, 1H), 8.48 (d, 1H). ESI-MS m/z: 546 (M+1), retention time 1.87.

Workup

  1. concentrationThe reaction was concentrated
  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)

Sources & evidence

ORD record
ord-21c418fcccf64a538eb45fcb7ff9f5de
Source dataset
uspto-grants-2007_09
Patent number
US07271176B2

Reaction notes

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