Triethylamine → HCID 86224995, compound

HRID 2389490Notes

Reaction equation

HRID 2389490 reaction equation
[C:1](Cl)(=[O:6])[CH2:2][CH2:3][CH2:4][CH3:5].[Cl:8][CH2:9][CH2:10][CH2:11][NH:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.CCN(CC)CC>ClCCl>[Cl:8][CH2:9][CH2:10][CH2:11][N:12]([CH2:13][CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[C:1](=[O:6])[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 61186Valeryl chlorideHCID 1948763-Chloro-N-(2-phenylethyl)propan-1-amine

Product 1

HCID 86224995HCID 86224995, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of valeryl chloride (342 mg, 338 μl, 2.83 mmol) in dichloromethane (6 ml) and cooled to 0° C. is added a solution of (3-chloro-propyl)-phenethyl-amine (Starting material Q-01e, 560 mg, 2.83 mmol). The colourless solution turns yellow and after 2 min, a solid crystallizes out. Upon dropwise addition of Et3N (315 mg, 409 μl, 2.83 mmol) the solution turns colourless again and the solid dissolves instantaneously. The mixture is allowed to stir for 4 h at which time yet again a solid had crystallized out. Saturated aqueous NH4Cl solution is added and the organic phase is washed once with some saturated aqueous NaHCO3 solution and dried over Na2SO4. The solvent is removed in vacuo and the residue is dried under high vacuum, yielding the title compound as an orange oil: tR=2.48 min (LC-2), ESI-MS (pos.): m/z 282.07 [M+H]+; 1H-NMR (CDCl3): δ (ppm) 0.86-0.97 (m, 3H, CH3), 1.23-1.44 (m, 4H, CH2CH3), 1.55 (quint., 1H, CH2CH2CH3), 1.65 (quint., 1H, CH2CH2CH3), 1.95 (quint., 2H, CH2CH2N), 2.03-2.19 (m, 2H, CH2C═O), 2.90 (t, 2H, CH2Ph), 3.35-3.59 (m, 6H), 7.15-7.34 (m, 2Harom).

Workup

  1. customa solid crystallizes out
  2. dissolutionthe solid dissolves instantaneously
  3. customhad crystallized out
  4. additionSaturated aqueous NH4Cl solution is added
  5. washthe organic phase is washed once with some saturated aqueous NaHCO3 solution
  6. dry with materialdried over Na2SO4
  7. customThe solvent is removed in vacuo
  8. customthe residue is dried under high vacuum

Sources & evidence

ORD record
ord-6054e9636e3f43738d5970d876fb261e
Source dataset
uspto-grants-2012_09
Patent number
US08273740B2

Reaction notes

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