Triethylamine → N-[2-Chloro-4-(tetrahydro-pyran-2-yloxy)-benzyl]-3,3-dimethyl-N-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-butyramide

HRID 1827536Notes

Reaction equation

HRID 1827536 reaction equation
[Cl:1][C:2]1[CH:23]=[C:22]([O:24][CH:25]2[CH2:30][CH2:29][CH2:28][CH2:27][O:26]2)[CH:21]=[CH:20][C:3]=1[CH2:4][NH:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH2:14][N:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)=[CH:8][CH:7]=1.C(N(CC)CC)C.[C:38]([CH2:42][C:43](Cl)=[O:44])([CH3:41])([CH3:40])[CH3:39].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[Cl:1][C:2]1[CH:23]=[C:22]([O:24][CH:25]2[CH2:30][CH2:29][CH2:28][CH2:27][O:26]2)[CH:21]=[CH:20][C:3]=1[CH2:4][N:5]([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH2:14][N:15]2[CH2:16][CH2:17][CH2:18][CH2:19]2)=[CH:8][CH:7]=1)[C:43](=[O:44])[CH2:42][C:38]([CH3:41])([CH3:40])[CH3:39]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 815143,3-Dimethylbutanoyl chlorideHCID 516892Sodium BicarbonateHCID 22137435(2-Chloro-4-(tetrahydro-pyran-2-yloxy)-benzyl]-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-amine

Product 1

HCID 22137420N-[2-Chloro-4-(tetrahydro-pyran-2-yloxy)-benzyl]-3,3-dimethyl-N-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-butyramide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [2-chloro-4-(tetrahydro-pyran-2-yloxy)-benzyl]-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl)-amine (0.100 g, 0.232 mmol) and triethylamine (0.100 mL, 0.696 mmol) in 2 mL methylene chloride was added tert-butylacetyl chloride (0.081 mL, 0.58 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 529.2 (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-4ed963e720144eb3a6aecf13a6369021
Source dataset
uspto-grants-2006_05
Patent number
US07053212B2

Reaction notes

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