Ethylamine hydrochloride → HCID 10225885, compound

HRID 1267509Notes

Reaction equation

HRID 1267509 reaction equation
Cl.[CH2:2]([NH2:4])[CH3:3].[OH-].[Na+].[CH2:7]([N:15]1[CH:20]2[CH2:21][CH2:22][CH:16]1[CH2:17][C:18](=[C:23]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:24]1[CH:32]=[CH:31][C:27]([C:28](Cl)=[O:29])=[CH:26][CH:25]=1)[CH2:19]2)[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C(Cl)Cl>[CH2:2]([NH:4][C:28](=[O:29])[C:27]1[CH:26]=[CH:25][C:24]([C:23](=[C:18]2[CH2:17][CH:16]3[N:15]([CH2:7][CH2:8][C:9]4[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=4)[CH:20]([CH2:21][CH2:22]3)[CH2:19]2)[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[CH:32][CH:31]=1)[CH3:3]

Participants

5

Reactant 3

HCID 11198Ethylamine hydrochlorideHCID 14798Sodium HydroxideHCID 18545696HCID 18545696, compound

Product 1

HCID 10225885HCID 10225885, compoundYield 27.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 11.4 g (0.14 mole) of ethylamine hydrochloride and 150 mL of 3N NaOH and 100 mL of CH2Cl2 were cooled in an ice bath. A solution of 4.7 g (0.015 mole) of 4-[(8-phenethyl-8-azabicyclo[3.2.1]oct-3-ylidene)phenylmethyl]benzoyl chloride prepared using Procedure E in 60 mL of CH2Cl2 was added. After the addition was complete, the ice bath was removed and the reaction stirred at room temperature for 2 h. The organics were separated off and washed with water, brine and dried (K2CO3). The solvent was evaporated in vacuo and converted to the HCl salt with Et2O/HCl to give 1.86 g of N-ethyl-4-[(8-phenethyl-8-azabicyclo[3.2.1]oct-3-ylidene)phenylmethyl]benzamide; mp 296-298° C. (Decomp). MS m/z (MH+) 451. 1H NMR (DMSO-d6) δ 8.5 (ar, 1H); 7.8 (d, 2H); 7.4-7.1 (ar, 12H); 4.05 (bs, 2H); 3.4-3.2 (m, 3H); 3.1 (s, 3H); 2.9 (d, 2H); 2.4 -2.1 (m, 4H); 1.8 (m, 2H); 1.1 (t, 3H).

Workup

  1. temperaturewere cooled in an ice bath
  2. additionwas added
  3. additionAfter the addition
  4. customthe ice bath was removed
  5. customThe organics were separated off
  6. washwashed with water, brine
  7. dry with materialdried (K2CO3)
  8. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-e4c2eee4668b4240bf18841542da523c
Source dataset
uspto-grants-2003_04
Patent number
US06552036B2

Reaction notes

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