Triethylamine → HCID 22137460, compound

HRID 1827564Notes

Reaction equation

HRID 1827564 reaction equation
[N:1]1([CH2:6][CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][CH:16]([C:21]3[CH:26]=[CH:25][C:24]([O:27][CH:28]4[CH2:33][CH2:32][CH2:31][CH2:30][O:29]4)=[CH:23][CH:22]=3)[CH2:17][CH2:18][CH2:19][CH3:20])=[CH:11][CH:10]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[C:41](Cl)(=[O:50])[CH2:42][CH2:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[C:44]1([CH2:43][CH2:42][C:41]([N:15]([C:12]2[CH:11]=[CH:10][C:9]([O:8][CH2:7][CH2:6][N:1]3[CH2:2][CH2:3][CH2:4][CH2:5]3)=[CH:14][CH:13]=2)[CH:16]([C:21]2[CH:22]=[CH:23][C:24]([O:27][CH:28]3[CH2:33][CH2:32][CH2:31][CH2:30][O:29]3)=[CH:25][CH:26]=2)[CH2:17][CH2:18][CH2:19][CH3:20])=[O:50])[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 64801Benzenepropanoyl chlorideHCID 516892Sodium BicarbonateHCID 22137457HCID 22137457, compound

Product 1

HCID 22137460HCID 22137460, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-{1-[4-(tetrahydro-pyran-2-yloxy)-phenyl]-pentyl}-amine (0.100 g, 0.22 mmol) and triethylamine (0.092 mL, 0.66 mmol) in 2 mL methylene chloride was added hydrocinnamoyl chloride (0.082 mL, 0.55 mmol), dropwise. The reaction mixture was stirred for 1 hr. at room temperature. Saturated aqueous sodium bicarbonate was added and the layers were separated. The aqueous layer was extracted with an additional 2 mL of methylene chloride. The combined organic layers were concentrated to give the title compound of Step A. MS 585.1 (M+1)+

Workup

  1. customat room temperature
  2. customthe layers were separated
  3. extractionThe aqueous layer was extracted with an additional 2 mL of methylene chloride
  4. concentrationThe combined organic layers were concentrated

Sources & evidence

ORD record
ord-7783670f28a24123981611f02dc90b12
Source dataset
uspto-grants-2006_05
Patent number
US07053212B2

Reaction notes

Loading…