Triethylamine → N-(3-isopropoxyphenylacetyl)-N-(2-methoxyethyl)-2-(3,4-dichlorophenyl)-4-(tetrahydropyran-2-yloxy)butylamine

HRID 742636Notes

Reaction equation

HRID 742636 reaction equation
F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.[CH3:28][O:29][CH2:30][CH2:31][NH:32][CH2:33][CH:34]([C:44]1[CH:49]=[CH:48][C:47]([Cl:50])=[C:46]([Cl:51])[CH:45]=1)[CH2:35][CH2:36][O:37][CH:38]1[CH2:43][CH2:42][CH2:41][CH2:40][O:39]1.C(N(CC)CC)C.[CH:59]([O:62][C:63]1[CH:64]=[C:65]([CH2:69][C:70](O)=[O:71])[CH:66]=[CH:67][CH:68]=1)([CH3:61])[CH3:60]>C(Cl)Cl>[CH:59]([O:62][C:63]1[CH:64]=[C:65]([CH2:69][C:70]([N:32]([CH2:33][CH:34]([C:44]2[CH:49]=[CH:48][C:47]([Cl:50])=[C:46]([Cl:51])[CH:45]=2)[CH2:35][CH2:36][O:37][CH:38]2[CH2:43][CH2:42][CH2:41][CH2:40][O:39]2)[CH2:31][CH2:30][O:29][CH3:28])=[O:71])[CH:66]=[CH:67][CH:68]=1)([CH3:61])[CH3:60]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 166389242-(3-(Propan-2-yloxy)phenyl)acetic acidHCID 19705336N-(2-methoxyethyl)-2-(3,4-dichlorophenyl)-4-(tetrahydropyran-2-yloxy)butylamine

Product 1

HCID 19705328N-(3-isopropoxyphenylacetyl)-N-(2-methoxyethyl)-2-(3,4-dichlorophenyl)-4-(tetrahydropyran-2-yloxy)butylamineYield 80.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.6 g of BOP are added to a solution cooled at 0° C. of 1.9 g of the product prepared in step 2, 1.2 g of triethylamine and 0.96 g of 3-isopropoxyphenylacetic acid in 50 ml of CH2Cl2. The reaction mixture is stirred for one hour and is then concentrated under vacuum. The residue is taken up in ethyl acetate, washed with water, dried over Na2SO4 and concentrated under vacuum. 2.2 g of the expected product is obtained, which is directly used in the next step.

Workup

  1. concentrationis then concentrated under vacuum
  2. washwashed with water
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-f7c32892a3fe4a978366814dc08f965b
Source dataset
uspto-grants-1996_09
Patent number
US05554763

Reaction notes

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