Diethyl Ether → HCID 22129671, compound

HRID 609866Notes

Reaction equation

HRID 609866 reaction equation
[CH:1]([O:4][C:5]1[CH:6]=[C:7]([CH2:11][C:12]([OH:14])=O)[CH:8]=[CH:9][CH:10]=1)([CH3:3])[CH3:2].C(N1C=CN=C1)(N1C=CN=C1)=O.[Cl:27][C:28]1[CH:29]=[C:30]([CH:35]([N:39]2[CH2:44][CH2:43][C:42]([OH:51])([C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=3)[CH2:41][CH2:40]2)[CH2:36][NH:37][CH3:38])[CH:31]=[CH:32][C:33]=1[Cl:34].C(OCC)C>O1CCCC1.ClCCl>[ClH:27].[Cl:27][C:28]1[CH:29]=[C:30]([CH:35]([N:39]2[CH2:40][CH2:41][C:42]([OH:51])([C:45]3[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=3)[CH2:43][CH2:44]2)[CH2:36][N:37]([CH3:38])[C:12](=[O:14])[CH2:11][C:7]2[CH:8]=[CH:9][CH:10]=[C:5]([O:4][CH:1]([CH3:2])[CH3:3])[CH:6]=2)[CH:31]=[CH:32][C:33]=1[Cl:34]

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 682631,1'-CarbonyldiimidazoleHCID 15434904HCID 15434904, compoundHCID 166389242-(3-(Propan-2-yloxy)phenyl)acetic acid

Product 1

HCID 22129671HCID 22129671, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
23 °C

Procedure

A solution of 3-isopropoxyphenylacetic acid (670 mg) and 1,1'carbonyldiimidazole (590 mg) in tetrahydrofuran (15 mL) was stirred at reflux for 0.5 hours. The reaction was cooled to 23° C. and treated with a solution of N-[2-(3,4-dichlorophenyl)-2-(4-hydroxy-4-phenylpiperdino)ethyl]methylamine (940 mg) in tetrahydrofuran (40 mL). The reaction was stirred at 23° C. for 18 hours. The reaction was evaporated to a gold oil. The oil was partitioned between diethylether (100 mL) and 1 N hydrochloric acid (150 mL). The organic layer was treated with hydrochloric acid (g)/ether and evaporated to give a yellow oil which was dissolved in dichloromethane (10 mL) and added dropwise to diethylether (500 mL). The title compound precipitated as a white solid (480 mg); mp 127-132° C.; MS: m/z=555(M+1); NMR: 1.23 (d,3), 1.25 (d,3), 1.75 (m,2), 2.4 (m,1), 2.7 (m,1), 2.83 (s,3), 3.13 (m,2), 3.43 (m,2), 3.54 (s,2), 3.73 (m,1), 4.52 (m,1), 5.37 (m,1), 6.38 (d,1), 6.66 (s,1,), 6.73 (d,1), 7.01 (m,3,), 7.22 (m,2,), 7.46 (d,2), 7.7 (s,2,), 8.05 (s,1), 11.73 (s,1). Analysis Calculated: C, 61.95; H, 6.37; N, 4.66; Found: C, 61.94; H, 6.3; N, 4.56.

Workup

  1. temperatureat reflux for 0.5 hours
  2. customThe reaction was evaporated to a gold oil
  3. customThe oil was partitioned between diethylether (100 mL) and 1 N hydrochloric acid (150 mL)
  4. additionThe organic layer was treated with hydrochloric acid (g)/ether
  5. customevaporated
  6. customto give a yellow oil which
  7. customThe title compound precipitated as a white solid (480 mg)

Sources & evidence

ORD record
ord-a5fb9eeeb06849febea8d0567713df68
Source dataset
uspto-grants-1999_12
Patent number
US05998444

Reaction notes

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