Triethylamine → HCID 86619162, compound

HRID 1068664Notes

Reaction equation

HRID 1068664 reaction equation
[C:1]1([CH2:7][C@H:8]2[CH2:13][C@H:12]([N:14]3[CH2:19][CH2:18]C(=C4C5C=CC=CC=5CCN5C=CN=C45)[CH2:16][CH2:15]3)[CH2:11][CH2:10][NH:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1[C:42]2[C:37](=[CH:38][C:39](C(O)=O)=C[CH:41]=2)C=C1.N1([OH:55])C2C=CC=CC=2N=N1.[N:56]([CH2:59][CH2:60][CH2:61]N=NCC)([CH3:58])C.C([N:68]([CH2:71]C)CC)C>C(Cl)Cl>[CH3:41][C:42]1[CH:37]=[CH:38][CH:39]=[C:60]([CH3:61])[C:59]=1[NH:56][C:58](=[O:55])[CH2:71][N:68]1[CH2:16][CH2:15][N:14]([C@@H:12]2[CH2:11][CH2:10][NH:9][C@@H:8]([CH2:7][C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH2:13]2)[CH2:19][CH2:18]1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 742801H-Indole-5-Carboxylic AcidHCID 757711-HydroxybenzotriazoleHCID 21043654HCID 21043654, compoundHCID 131722707HCID 131722707, compound

Product 1

HCID 86619162HCID 86619162, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

(±)-trans-6,11-dihydro-11-[1-[2-(phenylmethyl)-4-piperidinyl]-4-piperidinylidene]-5H-imidazo[2,1-b][3]benzazepine (0.00023 mol) was added to 1H-indole-5-carboxylic acid (±0.080 g) and 1H-benzotriazole-1-ol (0.060 g) in CH2Cl2 (3 ml). The mixture was stirred and cooled on an ice-bath, under N2 flow. Triethylamine (0.5 ml) was added dropwise. A solution of (CH3)2—N—(CH2)3—N═N—CH2—CH3 (0.080 g) in CH2Cl2 (5 ml) was added dropwise and the reaction mixture was allowed to warm to RT, under N2. The reaction mixture was stirred overnight. The solvent was evaporated and the residue was purified by HPLC (eluent gradient: (0.5% ammoniumacetate in H2O)/CH3OH/C3CN 70/15/15 upgrading over 0/50/50 to 0/0/100). The desired fractions were collected and the solvent was evaporated, yielding 0.040 g of (±)-trans-N-(2,6-dimethylphenyl)-4-[2-(phenylmethyl)-4-piperidinyl]-1-piperazineacetamide (comp. 81).

Workup

  1. temperaturecooled on an ice-bath, under N2 flow
  2. stirringThe reaction mixture was stirred overnight
  3. customThe solvent was evaporated
  4. customthe residue was purified by HPLC (eluent gradient: (0.5% ammoniumacetate in H2O)/CH3OH/C3CN 70/15/15 upgrading over 0/50/50 to 0/0/100)
  5. customThe desired fractions were collected
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-91f72585889144c5921becae1628d9fa
Source dataset
uspto-grants-2001_06
Patent number
US06251894B1

Reaction notes

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