Water → {4-[1-(2-Dimethylamino-acetyl)-piperidin-4-yl]-phenyl}-carbamic acid tert-butyl ester

HRID 1989062Notes

Reaction equation

HRID 1989062 reaction equation
[CH3:1][N:2]([CH2:4][C:5](Cl)=[O:6])[CH3:3].[C:8]([O:12][C:13](=[O:27])[NH:14][C:15]1[CH:20]=[CH:19][C:18]([CH:21]2[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)=[CH:17][CH:16]=1)([CH3:11])([CH3:10])[CH3:9].C(N(CC)CC)C.O>C(Cl)Cl>[C:8]([O:12][C:13](=[O:27])[NH:14][C:15]1[CH:20]=[CH:19][C:18]([CH:21]2[CH2:26][CH2:25][N:24]([C:5](=[O:6])[CH2:4][N:2]([CH3:3])[CH3:1])[CH2:23][CH2:22]2)=[CH:17][CH:16]=1)([CH3:11])([CH3:9])[CH3:10]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 70103442-(Dimethylamino)acetyl chlorideHCID 29948379tert-butyl N-[4-(piperidin-4-yl)phenyl]carbamate

Product 1

HCID 68679986{4-[1-(2-Dimethylamino-acetyl)-piperidin-4-yl]-phenyl}-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dimethylamino-acetyl chloride (0.14 g, 0.86 mmol) and (4-piperidin-4-yl-phenyl)-carbamic acid tert-butyl ester (0.20 g, 0.72 mmol) were combined in CH2Cl2 (5 mL) and triethylamine (0.21 g, 2.2 mmol) was added. After 6 h, water (5 mL) was added. The reaction mixture was extracted with CH2Cl2 (3×5 mL) and the combined organic extracts were dried (MgSO4) and concentrated. The compound was found to be unstable on silica and therefore carried on without further purification. 1H NMR (400 MHz, CDCl3) δ (ppm): 9.04 (s, 1H), 7.52 (d, 2H, J=8.5 Hz), 7.16 (d, 2H, J=8.5 Hz), 3.06 (s 2H), 2.76-2.82(m, 2H), 2.59-2.65 (m, 1H), 2.37 (s, 6H), 1.78-1.81 (m, 2H), 1.54-1.64 (m, 2H), 1.48 (s, 9H), 1.30 (br s, 2H).

Workup

  1. extractionThe reaction mixture was extracted with CH2Cl2 (3×5 mL)
  2. dry with materialthe combined organic extracts were dried (MgSO4)
  3. concentrationconcentrated
  4. customcarried on without further purification

Sources & evidence

ORD record
ord-0c7eddbd76f84d3496998d3df892c6c6
Source dataset
uspto-grants-2010_01
Patent number
US07642270B2

Reaction notes

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