Dichloromethane → N-[Chloro-4-(tetrahydro-pyran-2-yloxy)-benzyl]-3-methyl-N-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-benzamide

HRID 1827539Notes

Reaction equation

HRID 1827539 reaction equation
Cl[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]1([CH3:47])[CH:43]=[CH:42][CH:41]=[C:40]([C:44](Cl)=[O:45])[CH:39]=1.C(=O)(O)[O-].[Na+].C(Cl)[Cl:54]>>[Cl:54][CH:4]([N: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:44](=[O:45])[C:40]1[CH:41]=[CH:42][CH:43]=[C:38]([CH3:47])[CH:39]=1)[C:3]1[CH:20]=[CH:21][C:22]([O:24][CH:25]2[CH2:30][CH2:29][CH2:28][CH2:27][O:26]2)=[CH:23][CH:2]=1

Participants

6

Reactant 5

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 743753-Methylbenzoyl chlorideHCID 516892Sodium BicarbonateHCID 22137435(2-Chloro-4-(tetrahydro-pyran-2-yloxy)-benzyl]-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-amine

Product 1

HCID 22137439N-[Chloro-4-(tetrahydro-pyran-2-yloxy)-benzyl]-3-methyl-N-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-benzamide

Procedure

A solution of [2-chloro-4-(tetrahydro-pyran-2-yloxy)-benzyl]-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-amine (100 mg, 0.232 mmol) and triethylamine (0.100 mL, 0.696 mmol) in methylene chloride was added to m-toluenecarbonyl chloride (72 mg, 0.46 mmol). The reaction mixture was stirred at room temperature for 24 hr. Saturated aqueous sodium bicarbonate was added and the layers were separated. The aqueous layer was washed with 2 mL of methylene chloride. The combined organic layers were concentrated to give the title compound of Step A. MS 549.1 (M+1)+

Workup

  1. customthe layers were separated
  2. washThe aqueous layer was washed with 2 mL of methylene chloride
  3. concentrationThe combined organic layers were concentrated

Sources & evidence

ORD record
ord-5c80da1d9bd64702a1a6287a0ee3f4a1
Source dataset
uspto-grants-2006_05
Patent number
US07053212B2

Reaction notes

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