2-Naphthoxyacetic acid → 1,2,3,4-tetrahydro-5-methoxy-N-[2-(2-naphthalenyloxy)ethyl]-N-propyl-2-naphthalenamine

HRID 327589

Reaction equation

HRID 327589 reaction equation
O(CC(O)=O)C1C=CC=CC=1.[CH:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][C:13]=1[O:22][CH2:23][C:24](O)=O.[CH2:27]([NH:30][CH:31]1[CH2:40][CH2:39][C:38]2[C:33](=[CH:34][CH:35]=[CH:36][C:37]=2[O:41][CH3:42])[CH2:32]1)[CH2:28][CH3:29]>>[CH3:42][O:41][C:37]1[CH:36]=[CH:35][CH:34]=[C:33]2[C:38]=1[CH2:39][CH2:40][CH:31]([N:30]([CH2:24][CH2:23][O:22][C:13]1[CH:14]=[CH:15][C:16]3[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH:12]=1)[CH2:27][CH2:28][CH3:29])[CH2:32]2

Participants

4

Reactant 3

HCID 84222-Naphthoxyacetic acidHCID 19188Phenoxyacetic AcidHCID 102425482-Propylamino-5-methoxytetralin2×

Product 1

HCID 199265681,2,3,4-tetrahydro-5-methoxy-N-[2-(2-naphthalenyloxy)ethyl]-N-propyl-2-naphthalenamine

Procedure

In Example 29, phenoxyacetic acid was replaced with (2-naphthoxy)acetic acid and (-)-2-(N-n-propylamino)-5-methoxytetralin was replaced with (±)-2-(N-n-propylamino)-5-methoxytetralin. The resulting oil was subjected to flash chromatography (Silica: 8:2 pet ether/EtOAc) and the product showed characteristic peaks at: NMR (300 MHz, CDCl3) δ 7.8-6.6(m, 10H), 4.15(t, 2H), 3.8(S, 3H), 0.9(t, 3H).

Sources & evidence

ORD record
ord-ede8cac636874c9fad7af3f0d22ad6c7
Source dataset
uspto-grants-1993_12
Patent number
US05274003

Linked notes

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