Triethylamine → Morpholin-4-yl-(4-{[(7-nitro-1,2,3,4-tetrahydro-naphthalen-2-yl)-propyl-amino]-methyl}-piperidin-1-yl)-methanone

HRID 983471Notes

Reaction equation

HRID 983471 reaction equation
[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH:10]([N:14]([CH2:18][CH:19]3[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]3)[CH2:15][CH2:16][CH3:17])[CH2:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].C(N(CC)CC)C.[N:32]1([C:38](Cl)=[O:39])[CH2:37][CH2:36][O:35][CH2:34][CH2:33]1>C(Cl)Cl>[N:32]1([C:38]([N:22]2[CH2:21][CH2:20][CH:19]([CH2:18][N:14]([CH:10]3[CH2:9][CH2:8][C:7]4[C:12](=[CH:13][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=4)[CH2:11]3)[CH2:15][CH2:16][CH3:17])[CH2:24][CH2:23]2)=[O:39])[CH2:37][CH2:36][O:35][CH2:34][CH2:33]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 848104-Morpholinecarbonyl chlorideHCID 22560628(7-Nitro-1,2,3,4-tetrahydro-naphthalen-2-yl)-piperidin-4-ylmethyl-propyl-amine

Product 1

HCID 22560631Morpholin-4-yl-(4-{[(7-nitro-1,2,3,4-tetrahydro-naphthalen-2-yl)-propyl-amino]-methyl}-piperidin-1-yl)-methanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ice-cold solution of (7-nitro-1,2,3,4-tetrahydro-naphthalen-2-yl)-piperidin-4-ylmethyl-propyl-amine, as prepared in Example 4, (400 mg, 1.2 mmol) and triethylamine (170 μl, 1.4 mmol, 1.2 eq.) in methylene chloride (40 mL) under an inert atmosphere morpholine-4-carbonyl chloride (170 μL, 1.4 mmol) was added dropwise. The ice bath was removed and the reaction was stirred at room temperature for 4 h. The methylene chloride was washed 2 times with water (30 mL), dried (MgSO4), filtered, and concentrated to afford morpholin-4-yl-(4-{[(7-nitro-1,2,3,4-tetrahydro-naphthalen-2-yl)-propyl-amino]-methyl}-piperidin-1-yl)-methanone as a clear oil (540 mg).

Workup

  1. additionwas added dropwise
  2. customThe ice bath was removed
  3. washThe methylene chloride was washed 2 times with water (30 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e5ad8e84118841eab785717903519a4c
Source dataset
uspto-grants-2005_03
Patent number
US06864266B2

Reaction notes

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