Ammonium Hydroxide → HCID 10113006, compound

HRID 1267510Notes

Reaction equation

HRID 1267510 reaction equation
[CH2:1]([N:9]1[CH:14]2[CH2:15][CH2:16][CH:10]1[CH2:11][C:12](=[C:17]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:18]1[CH:26]=[CH:25][C:21]([C:22](Cl)=[O:23])=[CH:20][CH:19]=1)[CH2:13]2)[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[NH4+:33].[OH-]>>[CH2:1]([N:9]1[CH:14]2[CH2:15][CH2:16][CH:10]1[CH2:11][C:12](=[C:17]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:18]1[CH:26]=[CH:25][C:21]([C:22]([NH2:33])=[O:23])=[CH:20][CH:19]=1)[CH2:13]2)[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 14923Ammonium HydroxideHCID 18545696HCID 18545696, compound

Product 1

HCID 10113006HCID 10113006, compound

Procedure

A 1.5 g (0.0034 mole) sample of 4-[(8-phenethyl-8-azabicyclo[3.2.1]oct-3-ylidene)phenylmethyl]benzoyl chloride was cooled in an ice bath. 30 mL of NH4OH was added dropwise. The ice bath was removed and the mixture was stirred at room temperature for 2 h. The solid was filtered off and dried. The product was passed through a Biotage Flash 40 L (silica gel, 9:1; CH2Cl2:MeOH). Conversion to the HCl salt and recrystallization from EtOH/Et2O gave 0.45 g of 4-[(8-phenethyl-8-azabicyclo[3.2.1]oct-3-ylidene)phenylmethyl]benzamide; mp. 210-212° C. MS m/z (MH+) 423. 1H NMR (DMSO-d6) δ 7.95 (s, 1H); 7.9 (d, 2H); 7.4-7.2 (ar, 12H); 4.05 (bs, 1H); 3.6 (q, 2H); 2.9 (d, 2H); 2.4-2.1 (m, 5H); 1.8 (m, 3H); 1.1 (t, 3H).

Workup

  1. customThe ice bath was removed
  2. filtrationThe solid was filtered off
  3. customdried
  4. customConversion to the HCl salt and recrystallization from EtOH/Et2O

Sources & evidence

ORD record
ord-6b512abd180b4a03ad6b4f7639143828
Source dataset
uspto-grants-2003_04
Patent number
US06552036B2

Reaction notes

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